Pyridazin-3-one derivatives, their use, and intermediates for their production

ABSTRACT

Novel pyridazin-3-one derivatives of formula [1] are provided, which are useful as active ingredients of herbicides, wherein R 1  is haloalkyl; R 2  and R 3  are the same or different and are hydrogen, alkyl, haloalkyl, or alkoxyalkyl; and Q is [Q-1], [Q-2], [Q-3], [Q-4], or [Q-5]. Also provided are their use and intermediates for their production.

TECHNICAL FIELD

[0001] The present invention relates to pyridazin-3-one derivatives,their use as herbicides, and intermediates for their production.

BACKGROUND ART

[0002] EP-A-0029123 discloses a process for the preparation ofsubstituted anilines and novel substituted anilines. In particular, itteaches that certain substituted anilines obtained by this process areuseful as important starting materials for the preparation of novelsubstituted pyridazin-3-one derivatives having herbicidal activity inpostemergence application. These pyridazin-3-one derivatives are,however, different from those of the present invention in that they havea substituted phenoxyphenyl group as an essential structural element atposition 2 of the pyridazinone ring and further have quite distinctsubstituents on the pyridazinone ring.

DISCLOSURE OF INVENTION

[0003] The present inventors have intensively studied to find a compoundhaving excellent herbicidal activity. As a result, they have found thatpyridazin-3-one derivatives represented by formula [1] as depicted belowhave excellent herbicidal activity, thereby completing the presentinvention.

[0004] Thus the present invention provides a compound of the formula:

[0005] wherein R¹ is C₁-C₃ haloalkyl; R² and R³ are the same ordifferent and are hydrogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, or C₁-C₃alkoxy C₁-C₃ alkyl; and Q is [Q-1], [Q-2], [Q-3], [Q-4], or [Q-5] of theformula:

[0006] wherein

[0007] X is hydrogen or halogen;

[0008] Y is halogen, nitro, cyano, or trifluoromethyl;

[0009] Z¹ is oxygen, sulfur, or NH;

[0010] Z² is oxygen or sulfur;

[0011] n is 0 or 1;

[0012] B is hydrogen, halogen, nitro, cyano, chloroosulfonyl, OR¹⁰,SR¹⁰, SO₂—OR¹⁰, N(R¹¹)R¹², SO₂N(R¹¹)R¹², NR¹¹(COR¹³), NR¹¹(SO₂R¹⁴),N(SO₂R¹⁴)—(SO²R¹⁵), N(SO₂R¹⁴)(COR¹³), NHCOOR¹³, COOR¹⁰, CON(R¹¹)R¹²,CSN(R¹¹)R¹², COR¹⁶, CR¹⁷═CR¹⁸COR¹⁶, CR¹⁷═CR¹⁸COOR¹³,CR¹⁷═CR¹⁸CON(R¹¹)R¹², CH₂CH—WCOOR 13, CH₂CHWCON(R¹¹)R¹², CR¹⁷═NOR³³,CR¹⁷═NN(R¹¹)R¹², CR¹⁷(Z²-R³⁴)₂, OCO₂R¹⁹, or OCOR¹⁹;

[0013] R⁴ is hydrogen or C₁-C₃ alkyl;

[0014] R⁵ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈cycloalkylalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆haloalkynyl, cyano C₁-C₆ alkyl, C₂-C₈ alkoxyalkyl, C₃-C₈alkoxyalkoxyalkyl, carboxy C₁-C₆ alkyl, (C₁-C₆ alkoxy)-carbonyl C₁-C₆alkyl, ((C₁-C₄ alkoxy) C₁-C₄ alkoxy)carbonyl C₁-C₆ alkyl, (C₃-C₈cycloalkoxy)carbonyl C₁-C₆ alkyl, CH₂CON(R¹¹)R¹², CH₂COON(R¹¹)R¹²,CH(C₁-C₄ alkyl)CON(R¹¹)R¹², CH(C₁-C₄ alkyl)COON(R¹¹)R¹², C₂-C₈alkylthioalkyl, or hydroxy C₁-C₆ alkyl;

[0015] R⁶ is C₁-C₆ alkyl, C₁-C₆ haloalkyl, formyl, cyano, carboxyl,hydroxy C₁-C₆ alkyl, C₁-C₆ alkoxy C₁-C₆ alkyl, C₁-C₆ alkoxy C₁-C₆ alkoxyC₁-C₆ alkyl, (C₁-C₆ alkyl)carbonyloxy C₁-C₆ alkyl, (C₁-C₆haloalkyl)carbonyloxy C₁-C₆ alkyl. (C₁-C₆ alkoxy)carbonyl, or (C₁-C₆alkyl)carbonyl;

[0016] R⁷ is hydrogen or C₁-C₆ alkyl; and

[0017] R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, hydroxy C₁-C₆alkyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, (C₁-C₅alkyl)carbonyloxy C₁-C₆ alkyl, (C₁-C₆ haloalkyl)carbonyloxy C₁-C₆ alkyl,carboxyl, carboxy C₁-C₆ alkyl, (C₁-C₈ alkoxy)-carbonyl, (C₁-C₆haloalkoxy)carbonyl, (C₃-C₁₀ cycloalkoxy)carbonyl, (C₃-C₈alkenyl-oxy)carbonyl, (C₃-C₈ alkynyloxy)carbonyl, aminocarbonyl, (C₁-C₆alkyl)amino-carbonyl, di(C₁-C₆ alkyl)aminocarbonyl, (C₁-C₆alkyl)aminocarbonyloxy C₁-C₆ alkyl, or di(C₁-C₆ alkyl)aminocarbonyloxyC₁-C₆ alkyl;

[0018] wherein R¹⁰ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈cycloalkyl, benzyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl,C₃-C₆ haloalkynyl, cyano C₁-C₆ alkyl, C₂-C₈ alkoxyalkyl, C₂-C₈alkylthioalkyl, carboxy C₁-C₆ alkyl, (C₁-C₈ alkoxy)carbonyl C₁-C₆ alkyl,(C₁-C₆ haloalkoxy)carbonyl C₁-C₆ alkyl, ((C₁-C₄ alkoxy) C₁-C₄alkoxy)carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl,(C₁-C₆ alkyl)carbonyl C₁-C₆ alkyl, (C₁-C₆ haloalkyl)carbonyl C₁-C₆alkyl, {(C₁-C₄ alkoxy) C₁-C₄ alkyl}carbonyl C₁-C₆ alkyl, (C₃-C₈cycloalkyl)carbonyl C₁-C₆ alkyl, CH₂CON—(R¹¹)R¹², CH₂COON(R″)R¹²,CH(C₁-C₄ alkyl)CON(R″)R¹², CH(C₁-C₄ alkyl)-COON(R¹¹)R¹², {(C₁-C₆alkoxy)carbonyl C₁-C₆ alkyl}oxycarbonyl C₁-C₆ alkyl, or hydroxy C₁-C₆alkyl;

[0019] R¹¹ and R¹² are independently hydrogen, C₁-C₆ alkyl, C₁-C₆haloalkyl. C₃-C₆ alkenyl, C₃-C₆ alkynyl, cyano C₁-C₆ alkyl, C₂-C₈alkoxyalkyl, C₂-C₈ alkylthioalkyl, carboxy C₁-C₆ alkyl, (C₁-C₆alkoxy)carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkoxy)-carbonyl C₁-C₆ alkyl,{(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkyl, or R¹¹ and R¹² arecombined together to form tetramethylene, pentamethylene, orethyleneoxyethylene;

[0020] R¹³ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl,or C₃-C₆ alkenyl;

[0021] R¹⁴ and R¹⁵ are independently C₁-C₆ alkyl, C₁-C₆ haloalkyl, orphenyl optionally substituted with methyl or nitro;

[0022] R¹⁶ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl,C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, C₂-C₈ alkoxyalkyl,or hydroxy C₁-C₆ alkyl;

[0023] R¹⁷ and R¹⁸ are independently hydrogen or C₁-C₆ alkyl;

[0024] R¹⁹ is C₁-C₆ alkyl;

[0025] R³³ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl,cyano C₁-C₆ alkyl, or (C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl;

[0026] R³⁴ is C₁-C₆ alkyl, or two R³⁴'s are combined together to form(CH₂)₂ or (CH₂)₃; and

[0027] W is hydrogen, chlorine, or bromine,

[0028] (hereinafter referred to as the present compound(s)); and aherbicide containing it as an active ingredient.

[0029] The present invention also provides a compound of the formula:

[0030] wherein R³ is as defined above, and Q¹ is [Q¹-1], [Q-2], [Q¹-3],[Q-4], or [Q-5] of the formula:

[0031] wherein X, y, Z¹, Z², n, R⁴, R⁵, R⁷, and R⁸ are as defined above;B¹ is hydrogen, halogen, nitro, cyano, OR²⁷, SR²⁷, SO₂OR²⁷, NR¹¹(R¹²),SO₂NR¹¹(R¹²), NR¹¹—(COR¹³), NR¹¹(SO₂R¹⁴), N(SO₂R¹⁴)(SO₂R¹⁵),N(SO₂R¹⁴)(COR¹³), NHCOOR¹³, COOR²⁷, CONR¹¹(R¹²), CSNR¹¹(R¹²),CR¹⁷═CR¹⁸COOR¹³, CR¹⁷═CR¹⁸CONR¹—(R¹ 2), CH₂CHWCOOR¹³, CH₂CHWCONR¹¹(R¹²),CR¹⁷=NOR³³, CR¹⁷═NNR¹¹—(R¹²), CR¹⁷(Z²R³⁴)₂, OCO₂R¹⁹, or OCOR¹⁹; R⁹ isC₁-C₆ alkyl, C₁-C₆ haloalkyl, cyano, carboxyl, hydroxy C₁-C₆ alkyl,C₁-C₆ alkoxy C₁-C₆ alkyl, C₁-C₆ alkoxy C₁-C₆ alkoxy C₁-C₆ alkyl, (C₁-C₆alkyl)carbonyloxy C₁-C₆ alkyl, (C₁-C₆ haloalkyl)carbonyl-oxy C₁-C₆alkyl, (C₁-C₆ alkoxy)carbonyl, or (C₁-C₆ alkyl)carbonyl; wherein R¹⁹ isas defined above; R²⁷ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈cycloalkyl, benzyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl,C₃-C₆ haloalkynyl, cyano C₁-C₆ alkyl, C₂-C₈ alkoxyalkyl, C₂-Cgalkylthioalkyl, carboxy C₁-C₆ alkyl, (C₁-C₈ alkoxy)carbonyl C₁-C₆ alkyl,(C₁-C₆ haloalkoxy)carbonyl C₁-C₆ alkyl, {(C₁-C₄ alkoxy) C₁-C₄alkoxy}carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl,CH₂CON(R″)R¹², CH₂COON(R¹¹)R¹², CH(C₁-C₄ alkyl)CON(R¹¹)R¹², CH(C₁-C₄alkyl)COON(R¹¹)R¹², {(C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl}oxycarbonylC₁-C₆ alkyl, or hydroxy C₁-C₆ alkyl; and R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁷,R¹⁸, R¹⁹, R³³, R³⁴, and Z² are as defined above.

[0032] In the above definition of the present compounds, the respectivesubstituents are exemplified as follows:

[0033] Examples of the C₁-C₃ haloalkyl represented by R¹ includetrifluoromethyl and chlorodifluoromethyl.

[0034] Examples of the C₁-C₃ alkyl represented by R² and R³ includemethyl, ethyl, and isopropyl.

[0035] Examples of the C -C₃ haloalkyl represented by R² and R³ includetrichloromethyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl,and pentafluoroethyl.

[0036] Examples of the C₁-C₃ alkoxy C₁-C₃ alkyl represented by R² and R³include methoxymethyl.

[0037] Examples of the halogen represented by X, Y, and B includechlorine, fluorine, bromine, or iodine.

[0038] Examples of the C₁-C₆ alkyl represented by R¹⁰ include methyl,ethyl, isopropyl, propyl, isobutyl, butyl, t-butyl, amyl, isoamyl, andt-amyl.

[0039] Examples of the C₁-C₆ haloalkyl represented by R¹⁰ include2-chloroethyl, 3-chloropropyl, and 2,2,2-trifluoroethyl.

[0040] Examples of the C₃-C₈ cycloalkyl represented by R¹⁰ includecyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0041] Examples of the C₃-C₆ alkenyl represented by R¹⁰ include allyl,1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and2-methyl-3-butenyl.

[0042] Examples of the C₃-C₆ haloalkenyl represented by R¹⁰ include2-chloro-2-propenyl and 3,3-dichloro-2-propenyl.

[0043] Examples of the C₃-C₆ alkynyl represented by R¹⁰ includepropargyl, 1-methyl-2-propynyl, 2-butynyl, and 1,1-dimethyl-2-propynyl.

[0044] Examples of the C₃-C₆ haloalkynyl represented by R¹⁰ include4-bromo-2-butynyl.

[0045] Examples of the cyano C₁-C₆ alkyl represented by R¹⁰ includecyanomethyl Examples of the C₂-C₈ alkoxyalkyl represented by R¹⁰ includemethoxymethyl, methoxyethyl, ethoxymethyl, and ethoxyethyl.

[0046] Examples of the C₂-C₈ alkylthioalkyl represented by R¹⁰ includemethylthiomethyl.

[0047] Examples of the carboxy C₁-C₆ alkyl represented by R¹⁰ includecarboxymethyl, 1-carboxyethyl, and 2-carboxyethyl.

[0048] Examples of the (C₁-C₈ alkoxy)carbonyl C₁-C₆ alkyl represented byR¹⁰ include methoxycarbonylmethyl, ethoxycarbonylmethyl,propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl,isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl,isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl,1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl,1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl,1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl,1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and1-t-amyloxycarbonylethyl.

[0049] Examples of the (C₁-C₆ haloalkoxy)carbonyl C₁-C₆ alkylrepresented by R¹⁰ include 2-chloroethoxycarbonylmethyl.

[0050] Examples of the {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkylrepresented by R¹⁰ include methoxymethoxycarbonylmethyl and1-methoxymethoxycarbonylethyl.

[0051] Examples of the (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkylrepresented by R¹⁰ include cyclobutyloxycarbonylmethyl,cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl,1-cyclobutyloxycarbonylethyl, 1-cyclopentyloxycarbonylethyl, and1-cyclohexyloxycarbonylethyl.

[0052] Examples of the (C₁-C₆ alkyl)carbonyl C₁-C₆ alkyl represented byR¹⁰ include methylcarbonylmethyl.

[0053] Examples of the (C₁-C₆ haloalkyl)carbonyl C₁-C₆ alkyl representedby R¹⁰ include chloromethylcarbonylmethyl.

[0054] Examples of the {(C₁-C₄ alkoxy) C₁-C₄ alkyl}carbonyl C₁-C₆ alkyl,represented by R¹⁰ include 2-methoxyethylcarbonylmethyl.

[0055] Examples of the (C₃-C₈ cycloalkyl)carbonyl C₁-C₆ alkylrepresented by R¹⁰ include cyclopentylcarbonylmethyl.

[0056] Examples of the {(C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl}oxycarbonylC₁-C₆ alkyl represented by R¹⁰ include(ethoxycarbonyl)methoxycarbonylmethyl.

[0057] Examples of the C₁-C₆ alkyl represented by R¹¹ and R¹² includemethyl, ethyl, propyl, butyl, isopropyl, and isobutyl.

[0058] Examples of the C₁-C₆ haloalkyl represented by R¹¹ and R¹²include chloroethyl and bromoethyl.

[0059] Examples of the C₃-C₆ alkenyl represented by R¹¹ and R¹² includeallyl, 1-methyl-2-propenyl, and 3-butenyl.

[0060] Examples of the C₃-C₆ alkynyl represented by R¹I and R¹² includepropargyl and 1-methyl-2-propynyl.

[0061] Examples of the cyano C₁-C₆ alkyl represented by R¹¹ and R¹²include cyanomethyl.

[0062] Examples of the C₂-C₈ alkoxyalkyl represented by R¹ and R¹²include methoxymethyl and ethoxyethyl.

[0063] Examples of the C₂-C₈ alkylthioalkyl represented by R¹¹ and R¹²include methylthiomethyl and methylthioethyl.

[0064] Examples of the carboxy C₁-C₆ alkyl represented by R¹¹ and R¹²include carboxymethyl and 1-carboxyethyl.

[0065] Examples of the (C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl represented byR¹¹ and R¹² include methoxycarbonylmethyl, ethoxycarbonylmethyl,propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl,isobutoxycarbonylmethyl, t-butenyl, carbonylmethyl,amyloxycarbonylmethyl, isoamyloxycarbonylmethyl,t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl,1-propoxycarbonylethy, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl,1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl,1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and1t-amyloxycarbonylethyl.

[0066] Examples of the (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkylrepresented by R¹ and R¹² include cyclopentyloxycarbonylmethyl.

[0067] Examples of the ((C₁-C₄ alkoxy) C₁-C₄ alkoxy)carbonyl C₁-C₆ alkylrepresented by R¹¹ and R¹² include methoxymethoxycarbonylmethyl and1-methoxymethoxycarbonylethyl.

[0068] Examples of the C₁-C₆ alkyl represented by R¹³ include methyl,ethyl, propyl, butyl, amyl, isopropyl, isobutyl, and isoamyl.

[0069] Examples of the C₁-C₆ haloalkyl represented by R¹³ include2,2,2-trifluoroethyl.

[0070] Examples of the C₃-C₈ cycloalkyl represented by R¹³ includecyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0071] Examples of the C₃-C₆ alkenyl represented by R¹³ include allyl.

[0072] Examples of the C₁-C₆ alkyl represented by R¹⁴ and R¹⁵ includemethyl, ethyl, propyl, butyl, and isopropyl.

[0073] Examples of the C₁-C₆ haloalkyl represented by R¹⁴ and R¹⁵include trifluoromethyl, 2,2,2-trifluoroethyl, 2-chloroethyl,chloromethyl, and trichloromethyl.

[0074] Examples of the phenyl optionally substituted by methyl or nitro,which is represented by R¹⁴ and R¹⁵, include phenyl, p-methylphenyl,2-nitrophenyl, 3-nitrophenyl, and 4-nitrophenyl.

[0075] Examples of the C₁-C₆ alkyl represented by R¹⁶ include methyl,ethyl. propyl, butyl, amyl, isopropyl, isobutyl, t-butyl, isoamyl, andt-amyl.

[0076] Examples of the C₁-C₆ haloalkyl represented by R¹⁶ includechloromethyl, dichloromethyl, bromomethyl, dibromomethyl, 1-chloroethyl,1,1-dichloroethyl, 1-bromoethyl, and 1,1-dibromoethyl.

[0077] Examples of the C₂-C₆ alkenyl represented by R¹⁶ include vinyl,allyl, 1-propenyl, and 1-methyl-2-propenyl.

[0078] Examples of the C₂-C₆ haloalkenyl represented by R¹⁶ include3,3-dichloro-2-propenyl and 3,3-dibromo-2-propenyl.

[0079] Examples of the C₂-C₆ alkynyl represented by R¹⁶ include ethynyland 2-butynyl.

[0080] Examples of the C₂-C₆ haloalkynyl represented by R¹⁶ include3-bromo-2-propynyl.

[0081] Examples of the C₂-C₈ alkoxyalkyl represented by R¹⁶ includemethoxymethyl, ethoxymethyl, and isopropoxymethyl.

[0082] Examples of the hydroxy C₁-C₆ alkyl represented by R¹⁶ includehydroxymethyl.

[0083] Examples of the C₁-C₆ alkyl represented by R¹⁷ and R¹⁸ includemethyl.

[0084] Examples of the C₁-C₆ alkyl represented by R¹⁹ include methyl andethyl.

[0085] Examples of the C₁-C₆ alkyl represented by R³³ include methyl andethyl.

[0086] Examples of the C₁-C₆ haloalkyl represented by R³³ include2-chloroethyl.

[0087] Examples of the C₃-C₈ cycloalkyl represented by R³³ includecyclopentyl.

[0088] Examples of the C₃-C₆ alkenyl represented by R³³ include allyl.

[0089] Examples of the C₃-C₆ haloalkenyl represented by R³³ include2-chloro-2-propenyl.

[0090] Examples of the C₃-C₆ alkynyl represented by R³³ includepropargyl.

[0091] Examples of the C₃-C₆ haloalkynyl represented by R³³ include4-chloro-2-butynyl.

[0092] Examples of the cyano C₁-C₆ alkyl represented by R³³ include2-cyanoethyl and cyanomethyl.

[0093] Examples of the (C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl represented byR³³ include ethoxycarbonylmethyl.

[0094] Examples of the C₁-C₆ alkyl represented by R³⁴ include methyl andethyl.

[0095] Examples of the C₁-C₃ alkyl represented by R⁴ include methyl.

[0096] Examples of the C₁-C₆ alkyl represented by R⁵ include methyl,ethyl, propyl, butyl, amyl, isopropyl, isobutyl, and isoamyl.

[0097] Examples of the C₁-C₆ haloalkyl represented by R⁵ include2-chloroethyl, 2-bromoethyl, 3-chlorobutyl, 3-bromobutyl,difluoromethyl, and bromodifluoromethyl.

[0098] Examples of the C₃-C₈ cycloalkylalkyl represented by R⁵ includecyclopentyl-methyl.

[0099] Examples of the C₃-C₆ alkenyl represented by R⁵ include allyl,1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and2-methyl-3-butenyl.

[0100] Examples of the C₃-C₆ haloalkenyl represented by R⁵ include2-chloro-2-propenyl and 3,3-dichloro-2-propenyl.

[0101] Examples of the C₃-C₆ alkynyl represented by R⁵ includepropargyl, 1-methyl-2-propynyl, 2-butynyl, and 1,1-dimethyl-2-propynyl.

[0102] Examples of the C₃-C₆ haloalkynyl represented by R⁵ include3-iodo-2-propynyl and 3-bromo-2-propynyl.

[0103] Examples of the cyano C₁-C₆ alkyl represented by R⁵ includecyanomethyl.

[0104] Examples of the C₂-Cg alkoxyalkyl represented by R⁵ includemethoxymethyl, ethoxymethyl, and 1-methoxyethyl.

[0105] Examples of the C₃-Cg alkoxyalkoxyalkyl represented by R⁵ includemethoxyethoxymethyl.

[0106] Examples of the carboxy C₁-C₆ alkyl represented by RS includecarboxymethyl, 1-carboxyethyl, and 2-carboxyethyl.

[0107] Examples of the (C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl represented byR⁵ include methoxycarbonylmethyl, ethoxycarbonylmethyl,propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl,isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl,isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl,1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl,1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl,1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl,1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and1-t-amyloxycarbonylethyl.

[0108] Examples of the {(C₁-C₄ alkoxy) C₁-C₄ alkoxy)carbonyl C₁-C₆ alkylrepresented by R⁵ include methoxymethoxycarbonylmethyl and1-methoxymethoxycarbonylethyl.

[0109] Examples of the (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkylrepresented by R⁵ include cyclobutyloxycarbonylmethyl,cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl,1-cyclobutyloxycarbonylethyl, 1-cyclopentyloxycarbonylethyl, and1-cyclohexyloxycarbonylethyl.

[0110] Examples of the C₂-C₈ alkylthioalkyl represented by R⁵ includemethylthiomethyl.

[0111] Examples of the hydroxy C₁-C₆ alkyl represented by R⁵ includehydroxy-methyl, hydroxyethyl, and hydroxypropyl.

[0112] Examples of the C₁-C₆ alkyl represented by R⁶ include methyl andethyl.

[0113] Examples of the C₁-C₆ haloalkyl represented by R⁶ includebromomethyl, dibromomethyl, tribromomethyl, 1-bromoethyl, chloromethyl,dichloromethyl, and trichloromethyl.

[0114] Examples of the hydroxy C₁-C₆ alkyl represented by R⁶ includehydroxymethyl.

[0115] Examples of the C₁-C₆ alkoxy C₁-C₆ alkyl represented by R⁶include methoxymethyl, ethoxymethyl, propoxymethyl, andisopropoxymethyl.

[0116] Examples of the C₁-C₆ alkoxy C₁-C₆ alkoxy C₁-C₆ alkyl representedby R⁶ include methoxymethoxymethyl, methoxyethoxymethyl, andethoxymethoxymethyl.

[0117] Examples of the (C₁-C₆ alkyl)carbonyloxy C₁-C₆ alkyl representedby R⁶ include acetyloxymethyl, ethylcarbonyloxymethyl, andisopropylcarbonyloxymethyl.

[0118] Examples of the (C₁-C₆ haloalkyl)carbonyloxy C₁-C₆ alkylrepresented by R⁶ include trifluoroacetyloxymethyl,chloroacetyloxymethyl, and trichloroacetyloxymethyl.

[0119] Examples of the (C₁-C₆ alkoxy)carbonyl represented by R⁶ includemethoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl,amyloxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, andisoamyloxycarbonyl.

[0120] Examples of the (C₁-C₆ alkyl)carbonyl represented by R⁶ includemethylcarbonyl, ethylcarbonyl, and isopropylcarbonyl.

[0121] Examples of the C₁-C₆ alkyl represented by R⁷ include methyl.

[0122] Examples of the C₁-C₆ alkyl represented by R⁸ include methyl andethyl Examples of the C₁-C₆ haloalkyl represented by R⁸ includechloromethyl, bromomethyl, and fluoromethyl.

[0123] Examples of the C₁-C₆ hydroxyalkyl represented by R⁸ includehydroxymethyl.

[0124] Examples of the C₂-C₈ alkoxyalkyl represented by R⁸ includemethoxymethyl, ethoxymethyl, isopropoxymethyl, butoxymethyl, andisobutoxymethyl.

[0125] Examples of the C₃-C₁₀ alkoxyalkoxyalkyl represented by R⁸include methoxymethoxymethyl, methoxyethoxymethyl, andethoxymethoxymethyl.

[0126] Examples of the (C₁-C₅ alkyl)carbonyloxy C₁-C₆ alkyl representedby R⁸ include acetyloxymethyl, ethylcarbonyloxymethyl, andisopropylcarbonyloxymethyl.

[0127] Examples of the (C₁-C₆ haloalkyl)carbonyloxy C₁-C₆ alkylrepresented by R⁸ include 2-chloroethylcarbonyloxymethyl.

[0128] Examples of the carboxy C₁-C₆ alkyl represented by R⁸ includecarboxymethyl.

[0129] Examples of the (C₁-C₈)alkoxycarbonyl represented by R⁸ includemethoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl,amyloxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, andisoamyloxycarbonyl.

[0130] Examples of the (C₁-C₆ haloalkoxy)carbonyl represented by R⁸include 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl,3-chlorobutoxycarbonyl, 1-chloro-2-propoxycarbonyl,1,3-dichloro-2-propoxycarbonyl, 2,2-dichloroethoxycarbonyl,2,2,2-trifluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, and2,2,2-tribromoethoxycarbonyl.

[0131] Examples of the (C₃-C₁₀ cycloalkoxy)carbonyl represented by R⁸include cyclobutyloxycarbonyl, cyclopentyloxycarbonyl, andcyclohexyloxycarbonyl.

[0132] Examples of the (C₃-C₈ alkenyloxy)carbonyl represented by R⁸include allyloxycarbonyl and 3-butenyloxycarbonyl.

[0133] Examples of the (C₃-C₈ alkynyloxy)carbonyl represented by R⁸include propargyloxycarbonyl, 3-butynyloxycarbonyl, and1-methyl-2-propynyloxycarbonyl.

[0134] Examples of the (C₁-C₆ alkyl)aminocarbonyl represented by R⁸include methylaminocarbonyl, ethylaminocarbonyl, andpropylaminocarbonyl.

[0135] Examples of the di(C₁-C₆ alkyl)aminocarbonyl represented by R⁸include dimrethylaminocarbonyl, diethylaminocarbonyl, anddiisopropylaminocarbonyl.

[0136] Examples of the (C₁-C₆ alkyl)aminocarbonyloxy C₁-C₆ alkylrepresented by R⁸ include methylaminocarbonyloxymethyl,ethylaminocarbonyloxymethyl, and propyl-aminocarbonyloxymethyl.

[0137] Examples of the di(C₁-C₆ alkyl)aminocarbonyloxy C₁-C₆ alkylrepresented by R⁸ include dimethylaminocarbonyloxyalkyl anddiethylaminocarbonyloxyalkyl.

[0138] In the present compounds, preferred substituents from theviewpoint of their herbicidal activity are as follows:

[0139] R¹ is preferably methyl substituted with one or more fluorineatoms, such as trifluoromethyl or chlorodifluoromethyl, or ethylsubstituted with one or more fluorine atoms, such as pentafluoroethyl,and more preferably trifluoromethyl;

[0140] R² is preferably C₁-C₃ alkyl such as methyl or ethyl, orhydrogen, and more preferably methyl or hydrogen;

[0141] R³ is preferably C₁-C₃ alkyl such as methyl or ethyl, orhydrogen, and more preferably methyl or hydrogen; and

[0142] Q is preferably [Q-1], [Q-2], [Q-3], or [Q-4].

[0143] Preferred examples of the present compounds from the viewpoint oftheir herbicidal activity are those which contain the above preferredsubstituents in combination.

[0144] When Q is [Q-1], more preferred compounds are those wherein X ishydrogen or fluorine and Y is chlorine. Among these compounds are morepreferred ones wherein B is OR¹⁰, SR¹⁰, N(R¹¹)R¹², NR¹¹(SO₂R¹⁴), orCOOR¹⁰. Among these compounds are more preferred ones wherein R¹⁰ isC₁-C₆ alkyl, C₃-C₆ alkynyl, (C₁-C₈ alkoxy)carbonyl C₁-C₆ alkyl, or(C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl; R¹¹ is hydrogen; R¹² is (C₁-C₆alkoxy)carbonyl C₁-C₆ alkyl; and R¹⁴ is C₁-C₆ alkyl or C₁-C₆ haloalkyl.

[0145] When Q is [Q-2], more preferred compounds are those wherein X isfluorine or hydrogen; Z¹ is oxygen; R⁴ is hydrogen; and n is 1. Amongthese compounds are more preferred ones wherein R⁵ is C₃-C₆ alkynyl.

[0146] Typical examples of the preferred compounds are as follows:

[0147]7-Fluoro-6-(5-trifluoromethyl-3-pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one;

[0148]7-Fluoro-6-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one;

[0149]6-(5-Trifluoromethyl-3-pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one;

[0150]6-(4-Methyl-5-trifluoromethyl-3-pyridazinon-2-yl)-4-propargyl-2H-1-1,4-benzoxazin-3-one;

[0151] 2-(4-Chloro-2-fluoro-5-isopropoxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one;

[0152]2-(4-Chloro-2-fluoro-5-methoxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one;

[0153]2-(4-Chloro-2-fluoro-5-methoxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one;

[0154]2-(4-Chloro-2-fluoro-5-propargyloxyphenyl)-4-methyl-5-trifluoromethyl-pyridazin-3-one;

[0155] Methyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)-phenoxyacetate;

[0156] Ethyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)-phenoxyacetate;

[0157] Propyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)-phenoxyacetate;

[0158] Isopropyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate;

[0159] Butyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)-phenoxyacetate;

[0160] Pentyl2-chloro-4-fluoro-5-(4methyl-5-trifluoromethyl-3-pyridazinon-2-yl)-phenoxyacetate;

[0161] Cyclopentyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate;

[0162] Ethyl2-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxy}propionate;

[0163] Methyl2-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxy}propionate;

[0164] Ethyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylthioacetate;

[0165] Methyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)-phenylthioacetate;

[0166] Ethyl2-(2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate;

[0167] Methyl2-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate;

[0168] Methyl2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenoxy}propionate;

[0169] Ethyl2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenoxy}propionate;

[0170] Ethyl2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthioacetate;

[0171] Methyl2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthioacetate;

[0172] Ethyl2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate;

[0173] Methyl2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenyl-thio}propionate;

[0174] Isopropyl2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)-phenylthio}propionate;

[0175] Ethyl2-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylamino}propionate;

[0176] Ethyl2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylamino}propionate;

[0177] N-{2-chloro-4-fluoro-5-(4-methyl-5-trifluorormethyl-3-pyridazinon-2-yl)phenyl}methanesulfonamide;

[0178]N-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-y1)-phenyl}chloromethanesulfonamide;

[0179]N-(2-chloro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenyl-methanesulfonamide;

[0180] Methyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)benzoate;

[0181] Ethyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)-benzoate;

[0182] Ethyl2-chloro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)benzoate;

[0183] Isopropyl2-chloro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)benzoate; and

[0184]2-(4-Chloro-2-fluoro-5-propargyloxyphenyl)-6-methyl-5-trifluoromethylpyridazin-3-one.

[0185] Among these compounds, more preferred ones from the viewpoint oftheir herbicidal activity are as follows:

[0186]7-Fluoro-6-(5-trifluoromethyl-3-pyridazinon-2-yl)-4-proparygyl-2H-1,4-benzoxazin-3-one;

[0187]7-Fluoro-6-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one;

[0188] 6-(4-Methyl-5-trifluoromethyl-3-pyridazinon-2-yl)₄-propargyl-2H-1,4-benzoxazin-3-one;

[0189] Ethyl2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyrizazinon-2-yl)phenoxy}propionate;and

[0190] Ethyl2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate.

[0191] In addition, more preferred ones from the viewpoint of theirselectivity between crop plants and undesired weeds are as follows:

[0192]2-(4-Chloro-2-fluoro-5-propargyloxyphenyl)₄-methyl-5-trifluoromethylpyrizazin-3-one;

[0193] Ethyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)-phenoxyacetate;

[0194]N-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenyl}methanesulfonamide;and

[0195] Ethyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)-benzoate.

[0196] The present compounds can be produced, for example, according tothe production processes described below.

[0197] (Production Process I)

[0198] This is the production process in which among the presentcompounds, a compound of the formula:

[0199] wherein R¹. R², R³, and Q¹ are as defined above, is produced byreacting a hydrazone derivative of the formula:

[0200] wherein R¹, R³, and Q¹ are as defined above, with a compound ofthe formula:

[0201] wherein R² is as defined above; R²⁸ is C₁-C₆ alkyl such as methylor ethyl; and Ar is an optionally substituted phenyl such as phenyl.

[0202] The reaction is usually effected in a solvent. The reactiontemperature is usually in the range of −20° to 150° C., preferably 0° to100° C. The reaction time is usually in the range of a moment to 72hours. The amounts of the reagents to be used in the reaction, althoughthe proportion of 1 mole of compound [5] to 1 mole of compound [4] isideal, can be freely changed depending upon the reaction conditions.

[0203] Examples of the solvent which can be used include aliphatichydrocarbons such as hexane, heptane, ligroin, cyclohexane, andpetroleum ether; aromatic hydrocarbons such as benzene, toluene, andxylene; ethers such as diethyl ether, diisopropyl ether, dioxane,tetrahydrofuran (THF), and ethylene glycol dimethyl ether; nitrocompounds such as nitromethane and nitrobenzene; acid amides such asformamide, N,N-dimethylformamide, and acetamide; tertiary amines such aspyridine, triethylamine, diisopropylethylamine, N,N-dimethylaniline,N,N-diethylaniline, and N-methylmorpholine; sulfur compounds such asdimethylsulfoxide and sulforane; alcohols such as methanol, ethanol,ethylene glycol, and isopropanol; water; and mixtures thereof.

[0204] After completion of the reaction, the reaction solvent isdistilled out from the reaction mixture and the residue is subjected tochromatography, or the reaction mixture is subjected to ordinarypost-treatments such as extraction with an organic solvent andconcentration, followed by, if necessary, subsequent purification by atechnique such as chromatography or recrystallization. Thus the desiredcompound of the present invention can be isolated.

[0205] The above reaction is effected through a compound of the formula:

[0206] wherein R¹, R², R³, R²⁸, and Q¹ are as defined above.

[0207] This production process can also be conducted by isolatingcompound [6] and effecting intramolecular cyclization of compound [6].The cyclization can usually be effected in a solvent. The reactiontemperature is usually in the range of −20° to 150° C., preferably 50°to 150° C. The reaction time is usually in the range of a moment to 72hours.

[0208] Examples of the solvent which can be used include aliphatichydrocarbons such as hexane, heptane, ligroin, cyclohexane, andpetroleum ether; aromatic hydrocarbons such as benzene, toluene, andxylene; halogenated hydrocarbons such as chloroform, carbontetrachloride, dichloromethane, dichloroethane, chlorobenzene, anddichlorobenzene; ethers such as diethyl ether, diusopropyl ether,dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; ketonessuch as acetone, methyl ethyl ketone, methyl isobutyl ketone,isophorone, and cyclohexanone; esters such as ethyl formate, ethylacetate, butyl acetate, and diethyl carbonate; nitro compounds such asnitromethane and nitrobenzene; nitriles such as acetonitrile andisobutyronitrile; acid amides such as formamide, N,N-dimethylformamide,and acetamide; tertiary amines such as pyridine, triethylamine,diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, andN-methylmorpholine; sulfur compounds such as dimethylsulfoxide andsulforane; fatty acids such as formic acid, acetic acid, and propionicacid; alcohols such as methanol, ethanol, ethylene glycol, andisopropanol; water; and mixtures thereof.

[0209] As the reaction catalyst, acids such as sulfuric acid or basessuch as sodium methylate can be used.

[0210] (Production Process 2)

[0211] This is the production process according to the following scheme:

[0212] wherein R⁵¹ is a substituent other than hydrogen, which isincluded in the definition of R⁵; R¹, R², R³, R⁴, and X are as definedabove; R²² is C₁-C₆ alkyl; and D is chlorine, bromine, iodine,methanesulfonyloxy, trifluoromethanesulfonyloxy, orp-toluenesulfonyloxy.

[0213] Process for Producing Compound [8] from Compound [7]

[0214] Compound [8] can be produced by reacting compound [7] with anitrating agent in a solvent.

[0215] Nitrating agent: nitric acid or the like

[0216] Amount of nitrating agent: 1 to 10 moles per mole of compound [7]

[0217] Solvent: sulfuric acid

[0218] Temperature: -10° C. to room temperature

[0219] Time: a moment to 24 hours

[0220] Process for Producing Compound [9] from Compound [8]

[0221] Compound [9] can be produced by reacting compound [8] with acompound of the formula:

[0222] wherein R⁴ and R²² are as defined above, in the presence ofpotassium fluoride in a solvent.

[0223] Amount of compound [12]: 1 to 50 moles per mole of compound [8]

[0224] Amount of potassium fluoride: 1 to 50 moles per mole of compound[8]

[0225] Solvent: 1,4-dioxane or the like

[0226] Temperature: room temperature to refluxing temperature underheating

[0227] Time: a moment to 96 hours

[0228] Process for Producing Compound [10] from Compound [9]

[0229] Compound [10] can be produced by reducing compound [9] with ironpowder or the like in the presence of an acid in a solvent.

[0230] Amount of iron powder: 3 moles to an excess per mole of compound[9]

[0231] Acid: acetic acid or the like

[0232] Amount of acid: 1 to 10 moles

[0233] Solvent: water, ethyl acetate, or the like

[0234] Temperature: room temperature to refluxing temperature underheating

[0235] Time: a moment to 24 hours

[0236] Process for Producing Compound [11] from Compound [10]

[0237] Compound [11] can be produced by reacting compound [10] with acompound of the formula:

R⁵¹-D  [13]

[0238] wherein R⁵¹ and D are as defined above.

[0239] The reaction is usually effected in the presence of a base in asolvent. The reaction temperature is usually in the range of −20° to150° C., preferably 0° to 50° C. The reaction time is usually in therange of a moment to 48 hours. The amounts of the reagents to be used inthe reaction are usually 1 to 3 moles of compound [13] and usually 1 to2 moles of the base, per mole of compound [10].

[0240] Examples of the base which can be used include inorganic basessuch as sodium hydride, potassium hydride, sodium hydroxide, potassiumhydroxide, potassium carbonate, and sodium carbonate; and organic basessuch as triethylamine, diisopropylethylamine, pyridine,4-dimethylaminopyridine, N,N-dimethylaniline, and N,N-diethylaniline.

[0241] Examples of the solvent which can be used include aliphatichydrocarbons such as hexane, heptane, ligroin, cyclohexane, andpetroleum ether; aromatic hydrocarbons such as benzene, toluene, andxylene; halogenated hydrocarbons such as chlorobenzene anddichlorobenzene; ethers such as diethyl ether, diisopropyl ether,dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; nitrocompounds such as nitrobenzene; acid amides such as formamide,N,N-dimethylformamide, and acetamide; tertiary amines such as pyridine,triethylamine, diisopropylethylamine, N,N-dimethylamine,N,N-diethylaniline, and N-methylmorpholine; and mixtures thereof.

[0242] After completion of the reaction, the reaction mixture is pouredinto water, if necessary, and subjected to ordinary post-treatments suchas extraction with an organic solvent and concentration, followed by, ifnecessary, subsequent purification by a technique such as columnchromatography or recrystallization. Thus the present compound [11] canbe obtained.

[0243] The above compound [9] can also be produced according to thefollowing scheme:

[0244] wherein R¹, R², R³, R⁴, R²², and X are as defined above.

[0245] Process for Producing Compound [15] from Compound [14]

[0246] Compound [15] can be produced by reacting compound [14] with acompound of the formula:

[0247] wherein R⁴ and R²² are as defined above, in the presence of abase in a solvent.

[0248] Amount of compound [17]: 1 to 2 moles per mole of compound [14]

[0249] Base: sodium hydride, sodium carbonate, or the like Amount ofbase: 1 to 2 moles per mole of compound [14]

[0250] Solvent: 1,4-dioxane, N,N-dimethylformamide, or the like

[0251] Temperature: 0° to 100° C.

[0252] Time: a moment to 24 hours

[0253] Process for Producing Compound [9] from Compound [15]

[0254] Compound [9] can be produced by reacting compound [15] with anitrating agent in a solvent.

[0255] Nitrating agent: nitric acid or the like

[0256] Amount of nitrating agent: 1 to 10 moles per mole of compound[15]

[0257] Solvent: sulfuric acid, acetic-acid, or the like

[0258] Temperature: −10° C. to room temperature

[0259] Time: a moment to 24 hours

[0260] Process for Producing Compound [16] from Compound [14]

[0261] Compound [16] can be produced by reacting compound [14] with anitrating agent in a solvent.

[0262] Nitrating agent: nitric acid or the like

[0263] Amount of nitrating agent: 1 to 10 moles per mole of compound[14]

[0264] Solvent: sulfuric acid, acetic acid, or the like

[0265] Temperature: −10°0 C. to room temperature

[0266] Time: a moment to 24 hours

[0267] Process for Producing Compound [9] from Compound [16]

[0268] Compound [9] can be produced by reacting compound [16] withcompound[17] in the presence of a base in a solvent.

[0269] Amount of compound [17]: 1 to 2 moles per mole of compound [16]

[0270] Base: sodium hydride, potassium carbonate, or the like

[0271] Amount of base: 1 to 2 moles per mole of compound [16]

[0272] Solvent: 1,4-dioxane, N,N-dimethylformamide, or the like

[0273] Temperature: 0° to 100° C.

[0274] Time: a moment to 24 hours

[0275] (Production Process 3)

[0276] This is the production process according to the following scheme:

[0277] wherein X, R¹, R², R³, R⁵¹, and D are as defined above.

[0278] Process for Producing Compound [19] from Compound [18]

[0279] Compound [19] can be produced by reducing compound [18] with ironpowder or the like in the presence of an acid in a solvent.

[0280] Amount of iron powder: 3 moles to an excess per mole of compound[18]

[0281] Acid: acetic acid or the like

[0282] Amount of acid: 1 to 10 moles per mole of compound [18]

[0283] Solvent: water, ethyl acetate, or the like

[0284] Temperature: room temperature to refluxing temperature underheating

[0285] Time: a moment to 24 hours

[0286] Process for Producing Compound [21] from Compound [20]

[0287] Compound [20] can be produced by reacting compound [19] withsodium thiocyanate, potassium thiocyanate, or the like in a solvent, andthen reacting it with bromine or chlorine in a solvent.

[0288] Amount of sodium thiocyanate, potassium thiocyanate, or the like:1 to 10 moles per mole of compound [19]

[0289] Amount of bromine or chlorine: 1 to 10 moles per mole of compound[19]

[0290] Solvent: aqueous hydrochloric acid, aqueous acetic acid, aqueoussulfuric acid, or the like

[0291] Temperature: 0° to 50° C.

[0292] Time: a moment to 150 hours

[0293] Process for Producing Compound [21] from Compound [20]

[0294] Compound [21] can be produced by 1) reacting compound [20] withsodium nitrite, potassium nitrite, or the like in a solvent, and then 2)heating it in an acidic solution.

[0295] <Reaction 1)>

[0296] Amount of sodium nitrite, potassium nitrite, or the like: 1 to 2moles per mole of compound [20]

[0297] Solvent: aqueous hydrochloric acid or aqueous sulfuric acid

[0298] Temperature: −10° to 10° C.

[0299] Time: a moment to 5 hours

[0300] <Reaction 2)>

[0301] Acidic solution: aqueous hydrochloric acid, aqueous sulfuricacid, or the like

[0302] Temperature: 70° C. to refluxing temperature under heating

[0303] Time: a moment to 24 hours

[0304] Process for Producing Compound [22] from Compound [21]

[0305] Compound [22] can be produced by reacting compound [21] withcompound [13] in the presence of a base in a solvent.

[0306] Amount of compound [13]: 1 to 3 moles per mole of compound [21]

[0307] Base: sodium hydride, potassium carbonate, or the like

[0308] Amount of base: 1 to 2 moles per mole of compound [21]

[0309] Solvent: 1,4-dioxane, N,N-dimethylformamide, or the like

[0310] Temperature: 0° to 100° C.

[0311] Time: a moment to 48 hours

[0312] (Production Process 4)

[0313] This is the production process according to the following scheme:

[0314] wherein X, R¹, R², R³, and R⁵ are as defined above.

[0315] Process for Producing Compound [24]from Compound [23]

[0316] Compound [24] can be produced by reducing compound [23] with ironpowder or the like in the presence of an acid in a solvent.

[0317] Amount of iron powder: 3 moles to an excess per mole of compound[23]

[0318] Acid: acetic acid or the like

[0319] Amount of acid: 1 to 10 moles per mole of compound [23]

[0320] Solvent: water, ethyl acetate, or the like

[0321] Temperature: room temperature to refluxing temperature underheating

[0322] Time: a moment to 24 hours

[0323] Process for Producing Compound [25] from Compound [24]

[0324] Compound [25] can be produced by 1) reacting compound [24] with anitrite salt in a solvent to form a diazonium salt, and then 2) raisingthe temperature to cause the cyclization of the diazonium salt in asolvent.

[0325] <Reaction 1)>

[0326] Nitrite salt: sodium nitrite, potassium nitrite, or the like

[0327] Amount of nitrite salt: 1 to 2 moles per mole of compound [24]

[0328] Solvent: aqueous hydrochloric acid, aqueous sulfuric acid, or thelike

[0329] Temperature: -10° to IO° C.

[0330] Time: a moment to 5 hours

[0331] <Reaction 2)>

[0332] Solvent: aqueous hydrochloric acid, aqueous sulfuric acid, or thelike

[0333] Temperature: room temperature to 80° C.

[0334] Time: a moment to 24 hours

[0335] (Production Process 5)

[0336] This is the production process according to the following scheme:

[0337] wherein Y¹ is a substituent other than nitro, which is includedin the definition of Y; R¹⁰¹ is a substituent other than hydrogen, whichis included in the definition of R¹⁰; and X, R¹, R², and R³ are asdefined above.

[0338] Process for Producing Compound [27] from compound [26]

[0339] Compound [27] can be produced by adding nitric acid to compound[26] in a solvent (see Organic Synthesis Collective, Vol. 1, p. 372).

[0340] The reaction temperature is usually in the range of 0° to 100° C.The reaction time is usually in the range of a moment to 24 hours. Theamounts of the reagents to be used in the reaction, although theproportion of 1 mole of nitric acid to 1 mole of compound [26] is ideal,can be freely changed depending upon the reaction conditions.

[0341] Examples of the solvent which can be used include acidic solventssuch as sulfuric acid.

[0342] Process for Producing Compound [28] from compound [27]

[0343] Compound [28] can be produced by reducing compound [27] in asolvent (see Organic Synthesis Collective, Vol. 2, p. 471, and ibid.,Vol. 5, p. 829).

[0344] For example, the production can be achieved by adding compound[27], which is neat or dissolved in a solvent such as ethyl acetate, toa mixture of acetic acid, iron powder, and water. The reactiontemperature is usually in the range of 0° to 100° C. The reaction timeis usually in the range of a moment to 24 hours.

[0345] After completion of the reaction, the reaction mixture isfiltered to collect the crystals, which may be precipitated by theaddition of water, if necessary, or the reaction mixture is subjected toordinary post-treatments such as extraction with an organic solvent andconcentration, followed by, if necessary, subsequent purification by atechnique such as column chromatography or recrystallization. Thus thedesired product can be isolated.

[0346] Process for Producing Compound [29] from compound [28]

[0347] Compound [29] can be produced by 1) reacting compound [28] with anitrite salt in a solvent, and then 2) heating it in an acidic solvent.

[0348] <Reaction 1)>

[0349] Nitrite salt: sodium nitrite, potassium nitrite, or the likeAmount of nitrite salt: 1 to 2 moles per mole of compound [28]

[0350] Solvent: aqueous hydrochloric acid, aqueous sulfuric acid, or thelike

[0351] Temperature: −10° to 10° C.

[0352] Time: a moment to 5 hours

[0353] <Reaction 2)>

[0354] Acidic solvent: aqueous hydrochloric acid or aqueous sulfuricacid

[0355] Temperature: 70° C. to refluxing temperature under heating

[0356] Time: a moment to 24 hours.

[0357] Process for Producing Compound [30] from Compound [29]

[0358] Compound [30] can be produced by reacting compound [29] with acompound of the formula:

R¹⁰¹-D  [31]

[0359] wherein R¹⁰¹ and D are as defined above, in the presence of abase in a solvent.

[0360] The reaction is usually effected in a solvent. The reactiontemperature is usually in the range of −20° to 150° C., preferably 0° to100° C. The reaction time is usually in the range of a moment to 72hours. The amounts of the reagents to be used in the reaction, althoughthe proportion of 1 mole of compound [31] and 1 mole of a base to 1 moleof compound [29] is ideal, can be freely changed depending upon thereaction conditions.

[0361] Examples of the base which can be used include organic bases andinorganic bases such as potassium carbonate, sodium hydroxide, andsodium hydride.

[0362] Examples of the solvent which can be used include aliphatichydrocarbons such as hexane, heptane, ligroin, cyclohexane, andpetroleum ether; aromatic hydrocarbons such as benzene, toluene, andxylene; halogenated hydrocarbons such as chloroform, carbontetrachloride, dichloromethane, dichloroethane, chlorobenzene, anddichlorobenzene; ethers such as diethyl ether, diisopropyl ether,dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; ketonessuch as acetone, methyl ethyl ketone, methyl isobutyl ketone,isophorone, and cyclohexanone; esters such as ethyl formate, ethylacetate, butyl acetate, and diethyl carbonate; nitro compounds such asnitromethane and nitrobenzene, nitriles such as acetonitrile andisobutyronitrile; acid amides such as formamide, N,N-dimethylformamide,and acetamide; tertiary amines such as pyridine, triethylamine,diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, andN-methylmorpholine; sulfur compounds such as dimethylsulfoxide andsulforane; and mixtures thereof.

[0363] After completion of the reaction, the reaction mixture isfiltered to collect the crystals, which may be precipitated by theaddition of water, if necessary, or the reaction mixture is subjected toordinary post-treatments such as extraction with an organic solvent andconcentration, followed by, if necessary, subsequent purification by atechnique such as column chromatography or recrystallization. Thus thedesired product can be isolated.

[0364] (Production Process 6)

[0365] This is the production process according to the following scheme:

[0366] wherein R²³ and R²⁴ are independently a substituent other thanhydrogen, which is included in the definition of R¹¹ and R¹²; or COR³,SO₂R SO₂R¹⁵, or COOR¹⁰, wherein R¹⁰, R¹³, R¹⁴, and R¹⁵ are as definedabove; X, Y¹, R¹, R², and R³ are as defined above.

[0367] Process for Producing Compound [32]from Compound [28]

[0368] Compound [32] can be produced by reacting compound [28] with acompound of the formula:

R²⁰-D  [34]

[0369] wherein R²⁰ is a substituent other than hydrogen, which isincluded in the definition of R¹¹ or R¹²; or COR¹³, SO₂R¹⁴, SO₂R¹⁵, orCOOR¹⁰, wherein R¹⁰, R¹³, R¹⁴, and R¹⁵ are as defined above; and D is asdefined above; or with a compound of the formula:

(R²¹)₂O  [35]

[0370] wherein R²¹ is COR¹³, SO₂R¹⁴, SO₂R¹⁵, or COOR¹⁰, wherein R¹⁰, R³,R¹⁴, and R¹⁵ are as defined above, usually in the presence of a base andusually in a solvent.

[0371] The reaction temperature is usually in the range of −20° to 200°C., preferably 0° to 180° C. The reaction time is usually in the rangeof a moment to 72 hours. The amounts of the reagents to be used in thereaction, although the proportion of 1 mole of compound [34] or [35] to1 mole of compound [28] is ideal, can be freely changed depending uponthe reaction conditions.

[0372] Examples of the base which can be used include organic bases suchas pyridine and triethylamine, and inorganic bases.

[0373] Examples of the solvent which can be used include aliphatichydrocarbons such as hexane, heptane, ligroin, cyclohexane, andpetroleum ether; aromatic hydrocarbons such as benzene, toluene, andxylene; halogenated hydrocarbons such as chloroform, carbontetrachloride, dichloromethane, dichloroethane, chlorobenzene, anddichlorobenzene; ethers such as diethyl ether, diisopropyl ether,dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; ketonessuch as acetone, methyl ethyl ketone, methyl isobutyl ketone,isophorone, and cyclohexanone; esters such as ethyl formate, ethylacetate, butyl acetate, and diethyl carbonate; nitro compounds such asnitromethane and nitrobenzene; nitriles such as acetonitrile andisobutyronitrile; acid amides such as formamide, N,N-dimethylformamide,and acetamide; tertiary amines such, as pyridine, triethylamine,diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, andN-methylmorpholine; sulfur compounds such as dimethylsulfoxide andsulforane; and mixtures thereof.

[0374] After completion of the reaction, the reaction mixture isfiltered to collect the precipitated crystals, or the reaction mixtureis subjected to ordinary post-treatments such as extraction with anorganic solvent and concentration, followed by, if necessary, subsequentpurification by a technique such as column chromatography orrecrystallization. Thus the desired product can be isolated.

[0375] Process for Producing compound [33] from Compound [32]

[0376] Compound [33] can be produced by reacting compound [32] withcompound [34] or [35). This production process is based on the processfor producing compound [32] from compound [28].

[0377] (Production Process 7)

[0378] This is the production process according to the following scheme:

[0379] wherein X, Y, R¹, R², R³, R¹⁰, R¹¹, and R¹²are as defined above.

[0380] Process for Producing compound [37] from compound [36]

[0381] Compound [37] can be produced by reacting compound [36] withchlorosulfonic acid without any solvent or in a solvent.

[0382] Amount of chlorosulfonic acid: 1 mole to an excess per mole ofcompound [36]

[0383] Solvent: sulfuric acid

[0384] Temperature: 0° to 70° C.

[0385] Time: a moment to 24 hours (see Org. Syn. Coll., Vol. 1, 8(1941))

[0386] Process for Producing Compound [38] from Compound [37]

[0387] Compound [38] can be produced by reacting compound [37] with acompound of the formula:

R¹⁰-OH  [40]

[0388] wherein R¹⁰ is as defined above, in the presence of a basewithout any solvent or in a solvent.

[0389] Amount of compound [24]: 1 mole to an excess per mole of compound[37]

[0390] Base: organic bases such as triethylamine or inorganic bases suchas potassium carbonate

[0391] Amount of base: 1 to 2 moles per mole of compound [37]

[0392] Solvent: N,N-dimethylformamide, 1,4-dioxane, or the like

[0393] Temperature: 0° to 10° C.

[0394] Time: a moment to 24 hours

[0395] Process for Producing Compound [39] from Compound [37]

[0396] Compound [39] can be produced by reacting compound [37] with acompound of the formula:

R¹¹R¹²NH  [41]

[0397] wherein R¹¹ and R¹² are as defined above, in the presence orabsence of a base without any solvent or in a solvent.

[0398] Amount of compound [41]: 1 mole to an excess per mole of compound[37]

[0399] Base: organic bases such as triethylamine or inorganic bases suchas potassium carbonate

[0400] Amount of base: 1 to 2 moles per mole of compound [37]

[0401] Solvent: 1,4-dioxane, N,N-dimethylformamide, or the like

[0402] Temperature: 0° to 100° C.

[0403] Time: a moment to 24 hours

[0404] (Production Process 8)

[0405] This is the production process according to the following scheme:

[0406] wherein X, Y. R¹, R², R³, R¹¹, R¹², R¹⁷, R¹⁸, and R²² are asdefined above.

[0407] Process for Producing Compound [43] from Compound [42]

[0408] Compound [43] can be produced from compound [42] according to themethod described in JP-A 5-294920/1993, pp. 15-16.

[0409] Process for Producing Compound [44] from Compound [43]

[0410] Compound [44] can be produced by reacting compound [43] with acompound of the formula:

(C₆H₅)₃P═CR¹⁸COOR²²  [45]

or

(C₂H₅O)₂P(O)CHR¹⁸COOR²²  [46]

[0411] wherein R¹⁸ and R²² are as defined above, in a solvent, and whencompound [46] is used, in the presence of a base.

[0412] Amount of compound [45] or [46]: 1 to 2 moles per mole ofcompound [43]

[0413] Solvent: tetrahydrofuran, toluene, or the like

[0414] Base: sodium hydride or the like

[0415] Amount of base: 1 to 2 moles per mole of compound [43]

[0416] Temperature: 0° to 50° C.

[0417] Time: a moment to 24 hours

[0418] Process for Producing Compound 1451 from Compound [44]

[0419] Compound[45] can be produced by reacting compound [44] withcompound [41].

[0420] (Production Process 9)

[0421] This is the production process according to the following scheme:

[0422] wherein W² is chlorine or bromine; and X, Y, R¹, R², R³, and R¹³are as defined above.

[0423] The reaction conditions are described, for example, in U.S. Pat.No. 5,208,212.

[0424] The production can be achieved by converting compound [48] into adiazonium salt in a solution of hydrochloric acid, hydrobromic acid, orthe like according to the ordinary method, and then reacting it with acompound of the formula:

CH₂═CHCO₂R¹³  [50]

[0425] wherein R¹³ is as defined above, in the presence of a coppersalt, such as, copper (II) chloride or copper (II) bromide, in a solventsuch as acetonitrile.

[0426] The reaction temperature is usually in the range of −20° to 150°C., preferably 0° to 60° C. The reaction time is usually in the range ofa moment to 72 hours.

[0427] After completion of the reaction, the reaction mixture isfiltered to collect the crystals, which may be precipitated by theaddition of water, if necessary, or the reaction mixture is subjected toordinary post-treatments such as extraction with an organic solvent andconcentration, followed by, if necessary, subsequent purification by atechnique such as column chromatography or recrystallization. Thus thedesired product can be isolated.

[0428] (Production Process 10)

[0429] This is the production process according to the following scheme:

[0430] wherein W³ is bromine or iodine; and X, Y¹, R¹, R², R³, and R¹³are as defined above.

[0431] Process for Producing Compound [51] from compound [28]

[0432] Compound [51] can be produced by 1) making a diazonium salt fromcompound [28] in a solvent and then 2) reacting it with potassium iodideor copper (I) bromide in a solvent.

[0433] <Reaction I)>

[0434] Diazotizing agent: sodium nitrite, potassium nitrite, or thelike.

[0435] Amount of diazotizing agent: 1 to 2 moles per mole of compound[28]

[0436] Solvent: aqueous hydrogen bromide, aqueous sulfuric acid, or thelike.

[0437] Temperature: −10° to 10° C. Time: a moment to 5 hours

[0438] <Reaction 2)>

[0439] Amount of potassium iodide or copper (I) bromide: 1 mole to anexcess per mole of compound [28]

[0440] Solvent: aqueous hydrogen bromide, aqueous sulfuric acid, or thelike

[0441] Temperature: 0° to 80° C.

[0442] Time: a moment to 24 hours

[0443] (see Org. Syn. Coll., Vol. 2, 604 (1943), and ibid., Vol. 1, 136(1941))

[0444] Process for Producing Compound [52] from Compound [51]

[0445] Compound [52] can be produced by reacting compound [51] with acompound of the formula:

R¹³-OH  [53]

[0446] wherein R¹³ is as defined above, in the presence of a transitionmetal catalyst and a base in a solvent under an atmosphere of carbonmonoxide.

[0447] Catalyst: PdCl₂(PPh₃)₂ or the like

[0448] Amount of catalyst: a catalytic amount to 0.5 mole per mole ofcompound

[0449] Amount of compound [53]: 1 mole to an excess per mole of compound[51]

[0450] Base: organic bases such as diethylamine

[0451] Amount of base: 1 to 2 moles per mole of compound [51]

[0452] Solvent: N,N-dimethylformamide or the like

[0453] Pressure of carbon monoxide: 1 to 150 atm.

[0454] Temperature: 0° to 100° C.

[0455] Time: a moment to 72 hours

[0456] (see Bull. Chem. Soc. Jpn., 48 (7) 2075 (1975))

[0457] (Production Process 11)

[0458] This is the production process according to the following scheme:

[0459] wherein X, Y, R¹, R², R³, and R¹⁹ are as defined above.

[0460] Compound [55] can be produced by hydrolyzing compound [54] in anacid solvent such as sulfuric acid, or in the presence of an acid suchas boron tribromide in a solvent such as methylene chloride.

[0461] The reaction temperature is usually in the range of −20° to 150°C., preferably 0° to 100° C. The reaction time is usually in the rangeof a moment to 72 hours.

[0462] The amount of the acid to be used in the reaction, although theproportion of 1 mole of the acid to 1 mole of compound [54] is ideal,can be freely changed depending upon the reaction conditions.

[0463] After completion of the reaction, the reaction mixture isfiltered to collect the crystals, which may be precipitated by theaddition of water, if necessary, or the reaction mixture is subjected toordinary post-treatments such as extraction with an organic solvent andconcentration, followed by, if necessary, subsequent purification by atechnique such as column chromatography or recrystallization. Thus thedesired product can be isolated.

[0464] (Production Process 12)

[0465] This is the production process according to the following scheme:

[0466] wherein X, Y. R¹, R², R³, Z², and R¹⁷ are as defined above; Z³ isoxygen or sulfur; R²⁵ is hydrogen or C₁-C₅ alkyl; and R²⁶ is C₁-C₆alkyl, C₃-C₆ alkenyl, or C₃-C₆ alkynyl.

[0467] Compound [57] can be produced by reacting compound [56] with acompound of the formula:

[0468] ti R²⁶Z³H  [58]

[0469] wherein R²⁶ and Z³ are as defined above, in the presence orabsence of a catalyst and usually in a solvent.

[0470] The amount of compound [58] to be used in the reaction, althoughthe proportion of 1 mole of compound [58] to 1 mole of compound [56] isideal, can be freely changed depending upon the reaction conditions.

[0471] Examples of the catalyst which can be used includep-toluenesulfonic acid. Examples of the solvent which can be usedinclude toluene, xylene or the like, or compound [56].

[0472] The reaction temperature is usually in the range of 0° to 200°C., preferably 50° to 150° C. The reaction time is usually in the rangeof a moment to 72 hours.

[0473] After completion of the reaction, the reaction mixture isfiltered to collect the crystals, which may be precipitated by theaddition of water, if necessary, or the reaction mixture is subjected toordinary post-treatments such as extraction with an organic solvent andconcentration, followed by, if necessary, subsequent purification by atechnique such as column chromatography or recrystallization. Thus thedesired product can be isolated.

[0474] (Production Process 13)

[0475] This is the production process according to the following scheme:

[0476] wherein R⁶¹ is a substituent other than methyl, which is includedin the definition of R⁶; and X, Y, R¹, R², and R³ are as defined above.

[0477] Process for Producing Compound [59] from Compound [55]

[0478] Compound [59] can be produced by reacting compound [55] with2,3-dichloropropene in the presence of a base in a solvent.

[0479] Amount of 2,3-dichloropropene: 1 to 3 moles per mole compound[55]

[0480] Base: inorganic bases such as potassium carbonate

[0481] Amount of base: 1 to 2 moles per mole of compound [55]

[0482] Solvent: N,N-dimethylformamide or the like

[0483] Temperature: 0° to 70° C.

[0484] Time: a moment to 24 hours

[0485] Process for Producing Compound [60] from Compound [59]

[0486] Compound [60] can be produced by heating compound [59] in asolvent.

[0487] Solvent: N,N-dimethylformamide, N,N-dimethylaniline,N,N-diethylaniline, p-diisopropylbenzene, or the like

[0488] Temperature: 70° to 200° C.

[0489] Time: a moment to 24 hours

[0490] Process for Producing Compound [61] from Compound [60]

[0491] Compound (61] can be produced from compound [62] according to themethod in which the methyl group in position 2 on the benzofuran ring isreplaced with another substituent, as described in U.S. Pat. No.5,308,829, columns 2-11.

[0492] (Production Process 14)

[0493] This is the production process according to the following scheme:

[0494] wherein X, Y. R¹, R², R³, and R⁷ are as defined above.

[0495] Process for Producing Compound [62] from compound [55]

[0496] Compound [62] can be produced by reacting compound [55] with acompound of the formula:

CH₂═CR⁷CH₂W²  [65]

[0497] wherein W² and R⁷ are as defined above, in the presence of a basein a solvent.

[0498] Amount of compound [65]: 1 to 5 moles per mole of compound [55]

[0499] Base: inorganic bases such as potassium carbonate

[0500] Amount of base: 1 to 2 moles per mole of compound [55]

[0501] Solvent: N,N-dimethylformamide, 1,4-dioxane, or the like

[0502] Temperature: 0° to 70° C.

[0503] Time: a moment to 24 hours

[0504] Process for Producing Compound [63] from Compound [62]

[0505] Compound [64] can be produced by heating compound [62] in asolvent.

[0506] Solvent: N,N-dimethylaniline, N,N-diethylaniline,p-diisopropylbenzene, or the like

[0507] Temperature: 100° to 200° C.

[0508] Time: a moment to 24 hours

[0509] Process for Producing Compound [64] from Compound [63]

[0510] Compound [64] can be produced by heating compound [63] in thepresence of an acid in a solvent.

[0511] Acid: organic acids such as p-toluenesulfonic acid; and inorganicacids such as sulfuric acid

[0512] Amount of acid: a catalytic amount to 1 mole per mole of compound[63]

[0513] Solvent: toluene, xylene, or the like

[0514] Temperature: 100° to 250° C.

[0515] Time: a moment to 24 hours

[0516] (Production Process 15)

[0517] This is the production process according to the following scheme:

[0518] wherein R⁸¹ is a substituent other than methyl and hydroxymethyl,which is included in the definition of R⁸; and X, Y, R¹, R², R³, and R⁷are as defined above.

[0519] Process for Producing Compound [66] from Compound [63]

[0520] Compound [66] can be produced by reacting compound [63] with aperacid in a solvent.

[0521] Peracid: m-chloroperbenzoic acid or peracetic acid

[0522] Amount of peracid: 1 mole to an excess per mole of compound [63]

[0523] Solvent: halogenated hydrocarbons such as dichloromethane; andorganic acids such as acetic acid

[0524] Temperature: −20° C. to room temperature

[0525] Time: a moment to 24 hours

[0526] Process for Producing Compound [67] from Compound [66]

[0527] Compound [67] can be produced by reacting compound [66] in thepresence of a base in a solvent.

[0528] Base: potassium carbonate or the like

[0529] Amount of base: 1 to 2 moles per mole of compound [66]

[0530] Solvent: methanol, ethanol, or the like

[0531] Temperature: 0° to 50° C.

[0532] Time: a moment to 5 hours

[0533] Process for Producing Compound [68] from Compound [67]

[0534] Compound [68] can be produced from compound [67] according to themethod in which the hydroxyalkyl group in position 2 on thedihydrobenzofuran ring is replaced with another substituent, asdescribed in U.S. Pat. No. 5,411,935, columns 5-10.

[0535] (Production Process 16)

[0536] This is the production process according to the following scheme:

[0537] wherein WI is halogen, preferably chlorine; R³² is hydrogen orC₁-C₅ alkyl; and X, Y, Z², R¹, R², R³, R¹ R¹², R³³, and R³⁴ are asdefined above.

[0538] Process for Producing Compound [69] from compound [42]

[0539] Compound [69] can be produced by reacting compound [42] with ahalogenating agent such as thionyl chloride in a solvent according tothe ordinary method.

[0540] Process for Producing Compound [70] from Compound [69]

[0541] Compound [70] can be produced by reacting compound [69] with acompound of the formula:

[0542] wherein M^(⊕) is an alkali metal cation, preferably lithiumcation or sodium cation; and R¹⁹, R²², and R³² are as defined above, togive a compound of the formula:

[0543] wherein X, Y, R¹, R², R³, R¹⁹, R²², and R³² are as defined above,and then hydrolyzing and decarboxylating compound [75].

[0544] The first reaction is usually effected in a solvent. The reactiontemperature is usually in the range of −20° to 50° C., preferably roomtemperature. The reaction time is usually in the range of a moment to 72hours.

[0545] Examples of the solvent which can be used include aliphatichydrocarbons such as hexane, heptane, ligroin, cyclohexane, andpetroleum ether; ethers such as diethyl ether, diisopropyl ether,dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; acidamides such as formamide, N,N-dimethylformamide, and acetamide; sulfurcompounds such as dimethylsulfoxide and sulforane; and mixtures thereof.

[0546] The second reaction is effected in the presence of sulfuric acid,hydrobromic acid, or the like in a solvent such as a lower carboxylicacid, e.g., acetic acid, or without any solvent. The reactiontemperature is usually in the range of 80° to 1 40° C., preferably 100°to 120° C. The reaction time is usually in the range of a moment to 72hours.

[0547] Process for Producing Compound [71] from Compound [70]

[0548] Compound [71] can be produced by reacting compound [70] with acompound of the formula:

H₂N—O—R³³  [76]

[0549] wherein R³³ is as defined above.

[0550] The reaction is effected in a lower alcohol such as methanol,ethanol or isopropanol, or in a mixed solution of such a lower alcoholand water. The reaction temperature is in the range of 0° to 80° C. Thereaction time is in the range of a moment to 72 hours.

[0551] Compound [76] can be used in the form of a free base or an acidaddition salt such as a hydrochloride salt or a sulfate salt.

[0552] The above reaction can also be effected with the addition of abasic catalyst such as an organic base, e.g., pyridine; an alkali metalcarbonate, e.g., sodium carbonate, potassium carbonate or the like;alkali metal hydrogencarbonate; or alkaline earth metal carbonate.

[0553] Compound [71] can also be produced by reacting a compound of theformula:

[0554] wherein X, Y, R¹, R², R³, and R³² are as defined above, with acompound of the formula:

R³³-D  [78]

[0555] wherein R³³ and D are as defined above, in the presence of abase, usually in a solvent.

[0556] Examples of the base which can be used include alkali metalalcoholates and alkali metal hydrides such as sodium hydride.

[0557] The amounts of the reagents to be used in the reaction, althoughthe proportion of about 1 mole of compound [78] and 1 to 2 moles of thebase to 1 mole of compound [77] is ideal, can be free changed dependingupon the reaction conditions.

[0558] Examples of the solvent which can be used include ethers such asdiethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethyleneglycol dimethyl ether; acid amides such as formamide,N,N-dimethylformamide, and acetamide; sulfur compounds such asdimethylsulfoxide and sulforane; alcohols such as methanol, ethanol,ethylene glycol, and isopropanol; and mixtures thereof.

[0559] The reaction temperature in the above reaction is in the range of−10° to 100° C., preferably 0° to 80° C. The reaction time is in therange of a moment to 72 hours.

[0560] Process for Producing Compound [72] from compound [70]

[0561] Compound [72] can be produced by reacting compound [70] with acompound of the formula:

[0562] wherein R¹¹ and R¹² are as defined above.

[0563] The reaction is effected in a lower alcohol such as methanol,ethanol or isopropanol, or in a mixed solution of such a lower alcoholand water. The reaction temperature is in the range of 0° to 80° C. Thereaction time is in the range of a moment to 72 hours.

[0564] Compound [79] can be used in the form of a free base or an acidaddition salt such as a hydrochloride salt or a sulfate salt.

[0565] The above reaction can also be effected with the addition of abasic catalyst such as an organic base, e.g., pyridine; an alkali metalcarbonate, e.g., sodium carbonate, potassium carbonate or the like;alkali metal hydrogencarbonate; or alkaline earth metal carbonate.

[0566] Process for Producing Compound [73] from Compound [70]

[0567] Compound [73] can be produced by reacting compound [70] with acompound of the formula:

R³⁴-Z²H  [80]

[0568] wherein Z² and R³⁴ are as defined above, usually in the presenceof a catalytic amount to an excess of an acid such as p-toluenesulfonicacid, hydrochloric acid or sulfuric acid, in an organic solvent such asbenzene or chloroform.

[0569] The reaction temperature is in the range of −30° C. to theboiling temperature of the reaction mixture. The reaction time is in therange of a moment to 72 hours.

[0570] (Production Process 17)

[0571] This is the production process according to the following scheme:

[0572] wherein Q¹ and R¹ are as defined above.

[0573] Compound [82] can be produced by reacting compound [81] with acompound of the formula:

[0574] wherein R¹⁹ and R²² are as defined above, in a solvent.

[0575] The reaction temperature is usually in the range of 30° to 120°C., preferably 40° to 80° C. The reaction time is usually in the rangeof 5 to 72 hours. The amounts of the reagents to be used in thereaction, although the proportion of 1 mole of compound [83] to 1 moleof compound [81] is ideal, can be changed depending upon the reactionconditions.

[0576] Examples the solvent which can be used include tertiary aminessuch as triethylamine.

[0577] After completion of the reaction, the reaction solvent isdistilled out from the reaction mixture and the residue is subjected tochromatography, or the reaction mixture is subjected to ordinarypost-treatments such as extraction with an organic solvent andconcentration, followed by, if necessary, subsequent purification by atechnique such as column chromatography or recrystalhzation. Thus thedesired compound of the present invention can be isolated.

[0578] (Production Process 18)

[0579] This is the production process according to the following scheme:

[0580] wherein B³ is OR³⁵, SR³⁵, COOR³⁵, COR¹⁶, or CR¹⁷=CR¹⁸COR¹⁶(wherein R³⁵ is (C₁-C₆ alkylcarbonyl C₁-C₆ alkyl (C₁-C₆haloalkyl)carbonyl C₁-C₆ alkyl, (C₁-C₄ alkoxy) C₁-C₄ alkyl)carbonylC₁-C₆ alkyl, or (C₃-C₈ cycloalkyl)carbonyl C₁-C₆ alkyl; and R¹⁶, R¹⁷,and R¹⁸ are as defined above); B⁴ is asubstituent derived from B³ byprotecting its ketone or aldehyde moiety with an alcohol; and X, Y, R¹,R², and R³ are as defined above.

[0581] Process for Producing Compound [100] from Compound [99]

[0582] Compound [100] can be produced in the same manner as described inProduction Process 1, except that compound [99] is used in place ofcompound [4].

[0583] Process for Producing Compound [101] from Compound [100]

[0584] Compound [101] can be produced by deprotecting the ketal oracetal moiety of compound [100] by the ordinary method.

[0585] Compound [99] can be produced in the same manner as describedbelow in the production process for compound [4], except that the ketoneor aldehyde moiety in the substituent B³ of a compound of the formula:

[0586] wherein X, Y, and B³ are as defined above, is protected with analcohol such as methanol to give a compound of the formula:

[0587] wherein X, Y, and B⁴ are as defined above, and compound [103] isused in place of compound [91] as described below.

[0588] Compound [5], which is one of the starting compounds in theproduction of the present compounds by production process 1, can beobtained from commercial sources or can be produced, for example,according to the method described in Jikken Kagaku Kouza (Maruzen K.K.), 4th ed., Vol. 24, pp. 259-260.

[0589] Compound [4], which is the other starting compound used inproduction process 1, can be produced by reacting a compound of theformula:

[0590] wherein R¹ and R³ are as defined above; and V is iodine, bromine,or chlorine, with water in the presence of a base to give a compound ofthe formula:

[0591] R¹ CCR³ [85]

[0592] wherein R¹ and R³ are as defined above (hereinafter referred toas reaction 1), and then reacting compound [85] with a compound of theformula:

Q¹-NHNH₂  [86]

[0593] wherein Q¹ is as defined above (hereinafter referred to asreaction 2).

[0594] Compound [85] can also be reacted as its hydrate or acetalderivative in water or an alcohol.

[0595] Reaction 1 is usually effected in a solvent. The reactiontemperature is usually in the range of 20° to 100° C. The reaction timeis usually in the range of a moment to 24 hours. The amounts of thereagents to be used in the reaction, although the proportion of 2 molesof water and 2 moles of a base to 1 mole of compound [84] is ideal, canbe changed, if necessary.

[0596] Examples of the base which can be used include organic bases andinorganic bases such as sodium acetate and potassium acetate.

[0597] Examples of the solvent which can be used include aliphatichydrocarbons such as hexane, heptane, ligroin, cyclohexane, andpetroleum ether; aromatic hydrocarbons such as benzene, toluene, andxylene; halogenated hydrocarbons such as chlorobenzene anddichlorobenzene; ethers such as diethyl ether, diisopropyl ether,dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; esterssuch as ethyl formate, ethyl acetate, butyl acetate, and diethylcarbonate; nitro compounds such as nitromethane and nitrobenzene;nitriles such as acetonitrile and isobutyronitrile; acid amides such asN,N-dimethylformamide; tertiary amines such as pyridine, triethylamine,diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, andN-methylmorpholine; sulfur compounds such as dimethylsulfoxide andsulforane; alcohols such as methanol, ethanol, ethylene glycol, andisopropanol; water; and mixtures thereof.

[0598] Reaction 2 is usually effected in a solvent. The reactiontemperature is usually in the range of −20° to 200° C. The reaction timeis usually in the range of a moment to 72 hours. The amounts of thereagents to be used in the reaction, although the proportion of 1 moleof compound [86] to 1 mole of compound [84] used in reaction I is ideal,can be freely changed depending upon the reaction conditions. Ifnecessary, the hydrochloride salt or sulfate salt of compound [86] canalso be used.

[0599] Examples of the solvent which can be used include aliphatichydrocarbons such as hexane, heptane, ligroin, cyclohexane, andpetroleum ether; aromatic hydrocarbons such as benzene, toluene, andxylene; halogenated hydrocarbons such as chloroform, carbontetrachloride, dichloromethane, dichloroethane, chlorobenzene, anddichlorobenzene; ethers such as diethyl ether, diisopropyl ether,dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; esterssuch as ethyl formate, ethyl acetate, butyl acetate, and diethylcarbonate; nitro compounds such as nitromethane and nitrobenzene;nitriles such as acetonitrile and isobutyronitrile; acid amides such asformamide, N,N-dimethylformamide, and acetamide; tertiary amines such aspyridine, triethylamine, diisopropylethylamine, N,N-dimethylaniline,N,N-diethylaniline, and N-methylmorpholine; sulfur compounds such asdimethylsulfoxide and sulforane; fatty acids such as formic acid, aceticacid, and propionic acid; alcohols such as methanol, ethanol, ethyleneglycol, and isopropanol; water; and mixtures thereof.

[0600] After completion of the reaction, the reaction mixture isfiltered to collect the crystals, which may be precipitated by theaddition of water, if necessary, or the reaction mixture is subjected toordinary post-treatments such as extraction with an organic solvent andconcentration, followed by, if necessary, subsequent purification by atechnique such as column chromatography or recrystallization. Thus thedesired product can be isolated.

[0601] Among the examples of compound [4], a compound of the formula:

[0602] wherein X is as defined above; Y² is halogen; and B² is hydrogen,halogen, C₁-C₆ alkoxy, or C₁-C₆ alkylthio, can also be producedaccording to the following scheme:

[0603] wherein X, y², B², and R²² are as defined above.

[0604] Process for Producing Compound [89] from Compound [88]

[0605] Compound [89] can be produced by reacting compound [88] with anitrite salt in hydrochloric acid or sulfuric acid to convert it into adiazonium salt, and then reacting the diazonium salt with a compound ofthe formula:

[0606] wherein R²² is as defined above, in the presence of a base suchas sodium acetate or pyridine.

[0607] (see, e.g., Tetrahedron, Vol. 35, p. 2013 (1979))

[0608] Process for Producing Compound [90] from Compound [89]

[0609] Compound [90] can be produced by hydrolyzing compound [89]usually in the presence of a base in a solvent.

[0610] The reaction temperature is in the range of 0° to 150° C.,preferably 20° to 100° C. The reaction time is in the range of 1 to 24hours, preferably 1 to 10 hours. The amounts of the reagents to be usedin the reaction, although the proportion of 1 mole of a base to 1 moleof compound [89] is ideal, can be changed, if necessary.

[0611] Examples of the base which can be used include inorganic basessuch as potassium hydroxide, lithium hydroxide, barium hydroxide, andsodium hydroxide.

[0612] Examples of the solvent which can be used include aliphatichydrocarbons such as hexane, heptane, ligroin, cyclohexane, andpetroleum ether; aromatic hydrocarbons such as benzene, toluene, andxylene; halogenated hydrocarbons such as chlorobenzene anddichlorobenzene; ethers such as diethyl ether, diisopropyl ether,dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; ketonessuch as acetone, methyl ethyl ketone, methyl isobutyl ketone,isophorone, and cyclohexanone; nitro compounds such as nitromethane andnitrobenzene; acid amides such as N,N-dimethylformamide; tertiary aminessuch as pyridine, triethylamine, diisopropylethylamine,N,N-dimethylaniline, N,N-diethylaniline, and N-methylmorpholine; sulfurcompounds such as dimethylsulfoxide and sulforane; alcohols such asmethanol, ethanol, ethylene glycol, and isopropanol; water; and mixturesthereof.

[0613] Process for Producing Compound [87] from Compound [90]

[0614] Compound [87] can be produced by heating compound [90] in asolvent.

[0615] The reaction temperature is in the range of 50° to 200° C.,preferably 50° to 150° C. The reaction time is in the range of a momentto 72 hours.

[0616] Examples of the solvent which can be used include aliphatichydrocarbons such as hexane, heptane, ligroin, cyclohexane, andpetroleum ether; aromatic hydrocarbons such as benzene, toluene, andxylene; halogenated hydrocarbons such as chloroform, carbontetrachloride, dichloromethane, dichloroethane, chlorobenzene, anddichlorobenzene; ethers such as diethyl ether, diisopropyl ether,dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; ketonessuch as acetone, methyl ethyl ketone, methyl isobutyl ketone,isophorone, and cyclohexanone; esters such as ethyl formate, ethylacetate, butyl acetate, and diethyl carbonate; nitro compounds such asnitromethane and nitrobenzene; nitriles such as acetonitrile andisobutyronitrile; acid amides such as formamide, N,N-dimethylformamide,and acetamide; tertiary amines such as pyridine, triethylamine,diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, andN-methylmorpholine; sulfur compounds such as dimethylsulfoxide andsulforane; fatty acids such as formic acid, acetic acid, and propionicacid; alcohols such as methanol, ethanol, ethylene glycol, andisopropanol; water; and mixtures thereof.

[0617] The above reaction can also be effected with the use of a metal,e.g., copper, as a catalyst.

[0618] After completion of the reaction, the reaction mixture isfiltered to collect the precipitated crystals, or the reaction mixtureis subjected to ordinary post-treatments such as extraction with anorganic solvent and concentration, followed by, if necessary, subsequentpurification by a technique such as column chromatography orrecrystallization. Thus the desired compound can be isolated.

[0619] Compound [86] can also be produced by the following scheme:

[0620] wherein Q¹ is as defined above.

[0621] (see Organic Synthesis Collective, Vol. 1, p. 442)

[0622] Compound [91] is known in, or can be produced according to themethod as described in, EP-61741-A, U.S. Pat. Nos. 4,670,046, 4,770,695,4,709,049, 4,640,707, 4,720,927 , 5,169,431; and JP-A 63-156787/1988.

[0623] Some examples of compound [91] can also be produced according tothe following scheme:

[0624] wherein R³¹ is COR¹⁶ or COOR¹⁰.

[0625] Process for Producing Compound [95] from Compound [94]

[0626] Compound [95] can be produced by reacting compound [94] withnitric acid in a solvent.

[0627] The reaction temperature is usually in the range of 0° to 1001C.The reaction time is usually in the range of a moment to 24 hours. Theamounts of the reagents to be used in the reaction, although theproportion of 1 mole of nitric acid to 1 mole of compound [94] is ideal,can be freely changed depending upon the reaction conditions.

[0628] Examples of the solvent which can be used include acidic solventssuch as mixtures of nitric acid and sulfuric acid.

[0629] (see Organic Synthesis Collective, Vol. 1, p. 372)

[0630] Process for Producing Compound [96] from Compound [95]

[0631] Compound [96] can be produced by reducing compound [95] in amixture of acetic acid, iron powder, and water.

[0632] The reaction temperature is usually in the range of 0° to 100° C.The reaction time is usually in the range of a moment to 24 hours.

[0633] After completion of the reaction, the reaction mixture issubjected to ordinary post-treatments such as extraction with an organicsolvent and concentration, followed by, if necessary, subsequentpurification by a technique such as column chromatography orrecrystallization. Thus the desired compound can be isolated.

[0634] (see Organic Synthesis Collective, Vol. 2, p. 471, and ibid.,Vol. 5, p. 829)

[0635] The present compounds have excellent herbicidal activity, andsome of them exhibit excellent selectivity between crop plants andunfavorable weeds. In particular, the present compounds have herbicidalactivity against various unfavorable weeds as recited below, which maycause trouble in the foliar treatment and soil treatment on uplandfields.

[0636] Polygonaceae:

[0637] wild buckwheat (Polygonum convolvulus), pale smartweed (Polygonumlapathifolium), Pennsylvania smartweed (Polygonum pensylvanicum),ladysthumb (Polygonum persicaria), curly dock (Rumex crispus), broadleafdock (Rumex obtusifoltius), Japanese knotweed (Polygonum cuspidatum)

[0638] Portulacaceae:

[0639] common purslane (Portulaca oleracea)

[0640] Caryophyllaceae:

[0641] common chickweed (Stellaria media)

[0642] Chenopodiaceae:

[0643] common lambsquarters (Chenopodium album), kochia (Kochiascoparia)

[0644] Amaranthaceae:

[0645] redroot pigweed (Amaranthus retroflexus), smooth pigweed(Amaranthus hybridus)

[0646] Crusiferae:

[0647] wild radish (Raphatius raphaanistrum), wild mustard (Sinapisarvensis), shepherdspurse (Capsella buisa-pastorls)

[0648] Leguminosae:

[0649] hemp sesbania (Sesbania exaltata), sicklepod (Cassiaobtusifolia), Florida beggarweed (Desmodium tortuosum), white clover(Trifolium repens)

[0650] Malvaceae:

[0651] velvetleaf (Abutilon theophrasti), prickly sida (Sida spinosa)

[0652] Violaceae:

[0653] field pansy (Viola arvensis), wild pansy (Viola tricolor)

[0654] Rubiaceae:

[0655] catchweed bedstraw (cleavers) (Galium aparine)

[0656] Convolvulaceae:

[0657] ivyleaf morningglory (Ipomoea hederacea), tall morningglory(Ipomoea purpurea), entireleaf morningglory (Ipomoea hederacea var.integriuscula), pitted morningglory (Ipomoea lacunosa), field bindweed(Convolvulus arvensis)

[0658] Labiatae:

[0659] red deadnettle (Lamiumn purpureum), henbit (Lamium amplexicaule)

[0660] Solanaceae:

[0661] jimsonweed (Datura stramonium), black nightshade (Solanum nigrum)

[0662] Scrophulariaceae:

[0663] birdseye speedwell (Veronica persica), ivyleaf speedwell(Veronica hederaefolia)

[0664] Compositae:

[0665] common cocklebur (Xanthium pensylvanicum), common sunflower(Helianthus annuus), scentless chamomile (Matricaria perforata orinodora), corn marigold (Chrysantlhemum segetum), pineappleweed(Matricaria matricarioides), common ragweed (Ambrosia artemisiifolia),giant ragweed (Ambrosia trifida), horseweed (Erigeron canadensis),Japanese mugwort (Artemisia princeps), tall goldenrod (Solidagoaltissima)

[0666] Boraginaceae:

[0667] field forget-me-not (Myosotis arvensis)

[0668] Asclepiadaceae:

[0669] common milkweed (Asclepias syriaca)

[0670] Euphorbiaceae:

[0671] sun spurge (Euphorbia helioscopia), spotted spurge (Euphorbiamaculata)

[0672] Gramineae:

[0673] barnyardgrass (Echinochloa crus-galli), green foxtail (Setariaviridis), giant foxtail (Setaria faberi), large crabgrass (Digitariasanguinalis), goosegrass (Eleusine indica), annual bluegrass (Poaannua), blackgrass (Alopecurus myosuroides), wild oat (Avena fatua),johnsongrass (Sorghum halepense), quackgrass (Agropyron repens), downybrome (Bromus tectorum), bermudagrass (Cynodon dactylon), fall panicum(Panicum dichotomiflorum), Texas panicum (Panicum texanum), shattercane(Sorghum vulgare)

[0674] Commelinaceae:

[0675] common dayflower (Commelina communis)

[0676] Equisetaceae:

[0677] field horsetail (Equisetum arvense)

[0678] Cyperaceae:

[0679] rice flatsedge (Cyperus iria), purple nutsedge (Cyperusrotundus), yellow nutsedge (Cyperus esculentus)

[0680] Furthermore, some of the present compounds have no problematicphytotoxicity on main crops such as corn (Zea mays), wheat (Triticumaestivum), barley (Hordeum vulgare), rice (Oryza sativa), sorghum(Sorghum bicolor), soybean (Glycine max), cotton (Gossypium spp.), sugarbeet (Beta vulgaris), peanut (Arachis hypogaea), sunflower (Helianthusannuus) and canola (Brassica napus); garden crops such as flowers andornamental plants; and vegetable crops.

[0681] The present compounds can attain effective control of unfavorableweeds in the no-tillage cultivation of soybean (Glycine max), corn (Zeamays), and wheat (Triticum aestivum). Furthermore, some of them exhibitno problematic phytotoxicity on crop plants.

[0682] The present compounds have herbicidal activity against variousunfavorable weeds as recited below under the flooding treatment on paddyfields.

[0683] Gramineae:

[0684] barnyardgrass (Echinochloa oryzicola)

[0685] Scrophulariaceae:

[0686] common falsepimpernel (Lindernia procumbens)

[0687] Lythraceae:

[0688]Rotala indica, Ammannia mulaflora

[0689] Elatinaceae:

[0690]Elatine triandra

[0691] Cyperaceae:

[0692] smallflower umbrellaplant (Cyperus difformis), hardstem bulrush(Scirpus juncoides), needle spikerush (Eleocharis acicularis), Cyperusserotinus, Eleocharis kuroguwai

[0693] Pontedenraceae:

[0694]Monochoria vaginalis

[0695] Alismataceae:

[0696]Sagittaria pygmaea, Sagittaria trifolia, Alisma canaliculatum

[0697] Potamogetonaceae:

[0698] roundleaf pondweed (Potamogeton distinctus)

[0699] Umbelliferae:

[0700]Oenanthe javanica

[0701] Furthermore, some of the present compounds have no problematicphytotoxicity on transplanted paddy ice.

[0702] The present compounds can attain effective control of variousunfavorable weeds in orchards, grasslands, lawns, forests, waterways,canals, or other noncultivatedlands.

[0703] The present compounds also have herbicidal activity againstvarious aquatic plants such as water hyacinth (Eichhornia craissipes),which will grow in waterways, canals, or the like.

[0704] The present compounds have substantially the same characteristicsas those of the herbicidal compounds described in the publication ofInternational Patent Application, WO95/34659. In the case where cropplants with tolerance imparted by introducing a herbicide tolerance genedescribed in the publication are cultivated, the present compounds canbe used at greater doses than those used when ordinary crop plantswithout tolerance are cultivated, and it is, therefore, possible toattain effective control of other unfavorable plants.

[0705] When the present compounds are used as active ingredients ofherbicides, they are usually mixed with solid or liquid carriers ordiluents, surfactants, and other auxiliary agents to give formulationssuch as emulsifiable concentrates, wettable powders, flowables,granules, concentrated emulsions, and water-dispersible granules.

[0706] These formulations may contain any of the present compounds as anactive ingredient at an amount of 0.001% to 80% by weight, preferably0.005% to 70% by weight, based on the total weight of the formulation.

[0707] Examples of the solid carrier or diluent may include fine powdersor granules of the following materials: mineral matters such as kaolinclay, attapulgite clay, bentonite, terra alba, pyrophyllite, talc,diatomaceous earth, and calcite; organic substances such as walnut shellpowder; water-soluble organic substances such as urea; inorganic saltssuch as ammonium sulfate; and synthetic hydrated silicon oxide. Examplesof the liquid carrier or diluent may include aromatic hydrocarbons suchas methylnaphthalene, phenylxylylethane, and alkylbenzenes (e.g.,xylene); alcohols such as isopropanol, ethylene glycol, and2-ethoxyethanol; esters such as phthalic acid dialkyl esters; ketonessuch as acetone, cyclohexanone, and isophorone; mineral oils such asmachine oil; vegetable oils such as soybean oil and cotton seed oil;dimethylsulfoxide, N,N-dimethylformamide, acetonitrile,N-methylpyrrolidone, water, and the like.

[0708] Examples of the surfactant used for emulsification, dispersing,or spreading may include surfactants of the anionic type, such asalkylsulfates, alkylsulfonates, alkylarylsulfonates,dialkylsulfosuccinates, and phosphates of polyoxyethylene alkyl arylethers; and surfactants of the nonionic type, such as polyoxyethylenealkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylenepolyoxypropylene block copolymers, sorbitan fatty acid esters, andpolyoxyethylene sorbitan fatty acid esters.

[0709] Examples of the auxiliary agent used for formulation may includelignin-sulfonates, alginates, polyvinyl alcohol, gum arabic,carboxymethyl cellulose (CMC), and isopropyl acid phosphate (PAP).

[0710] The present compounds are usually formulated as described aboveand then used for the pre- or post-emergence soil, foliar, or floodingtreatment of unfavorable weeds. The soil treatment may include soilsurface treatment and soil incorporation. The foliar treatment mayinclude application over the plants and directed application in which achemical is applied only to the unfavorable weeds so as to keep off thecrop plants.

[0711] The present compounds can be used, if necessary, in combinationwith other compounds having herbicidal activity. Examples of thecompounds which can be used in combination with the present compoundsmay include various compounds described in Catalog 1995 Edition of FarmChemicals Handbook (Meister Publishing Company); AG CHEM NEW COMPOUNDREVIEW, VOL. 13, 1995 (AG CHEM INFORMATION SERVICE); or JOSOUZAI KENKYUSOURAN (Hakuyu-sha). Typical examples of such compounds are as follows:atrazin, cyanazine, dimethametryn, metribuzin, prometryn, simazine,simetryn, chlorotoluron, diuron, dymuron, fluometuron, isoproturon,linuron, methabenzthiazuron, bromoxynil, ioxynil, ethalfluralin,pendimethalin, trifluralin, acifluorfen, acifluorfen-sodium, bifenox,chlomethoxynil, fomesafen, lactofen, oxadiazon, oxyfluorfen,carfentrazone, flumiclorac-pentyl, flumioxazine, fluthiacet-methyl,sulfentrazone, thidiazimin, difenzoquat, diquat, paraquat, 2,4-D,2,4-DB, DCPA, MCPA, MCPB, clomeprop, clopyralid, dicamba, dithiopyr,fluroxypyr, mecoprop, naploanilide, phenothiol, quinclorac, triclopyr,acetochlor, alachlor, butachlor, diethatylethyl, metolachlor,pretilachlor, propachlor, bensulfuron-methyl, chlorsulfuron.chlorimuron-ethyl, halosulfuron-methyl, metsulfuron-methyl,nicosulfuron, pnumisulfuron, pyrazosulfuron-ethyl, sulfometuron-methyl,thifensulfuron-methyl, triasuifuron, tribenuron-methyl, azimsulfuron,cloransulam-methyl, cyclosulfamuron, flumeturam, flupyrsulfuron,flazasulfuron, imazosulfuron, metosularn, prosulfuron, nimsulfuron,triflusulfuron-methyl, imazamethabenz-methyl, imazapyr, imazaquin,imazethapyr, imazameth, imazamox, bispyribac-sodium, pyriminobac-methyl,pyrithiobac-sodium, alloxydimsodium, clethodim, sethoxydim, tralkoxydim,diclofop-methyl, fenoxaprop-ethyl, fenoxaprop-p-ethyl, fluazifop-butyl,fluazifop-p-butyl, haloxyfop-methyl, quizalofop-p-ethyl,cyhalofop-butyl, clodinafop-propargyl, benzofenap, clomazone,diflufenican, norflurazon, pyrazolate, pyrazoxyfen, isoxaflutole,sulcotrione, glufosinate-ammonium, glyphosate, bentazon, benthiocarb,bromobutide, butamifos, butylate, dimepiperate, dimethenamid, DSMA,EPTC, esprocarb, isoxaben, mefenacet, molinate, MSMA, piperophos,pributycarb, propanil, pyridate, triallate, cafenstrol, flupoxam, andthiafluamide.

[0712] The following will describe typical examples of such acombination, where the present compounds are designated by theircompound numbers shown in Tables 1 to 5.

[0713] 1. A mixture of one compound selected from the group consistingof compounds 1-495, 1-496, 1-499, 1-503 and 1-577, and one compoundselected from the group consisting of atrazin, cyanazine, bromoxynil andbentazon at a weight ratio of 1:1 to 100.

[0714] 2. A mixture of one compound selected from the group consistingof compounds 1-495, 1-496, 1-499, 1-503 and 1-577, and one compoundselected from the group consisting of clethodim, sethoxydim,dichlofop-methyl, quizalofop-p-ethyl, lactofen, acifluorfen,acifluorfen-sodium, fomesafen, flumiclorac-pentyl and dicamba at aweight ratio of 1:0.5 to 50.

[0715] 3. A mixture of one compound selected from the group consistingof compounds 1-495, 1-496, 1-499, 1-503 and 1-577, and one compoundselected from the group consisting of nicosulfuron, primisulfuron,prosulfuron, chlorimuran-ethyl, thifensulfuron, rimsulfuron,halosulfuron, oxasulfuron, isoxaflutole, imazethapyr and imazamox at aweight ratio of 1:0.1 to 10.

[0716] 4. A mixture of one compound selected from the group consistingof compounds 1-439, 1-482, 1-486, 1-496, 1-1076, 1-1123 and 1-1441, andone compound selected from the group consisting of isoproturon andchlorotoluron at a weight ratio of 1:1 to 100.

[0717] 5. A mixture of one compound selected from the group consistingof compounds 1-439, 1-482, 1-486, 1-496, 1-1076, 1-1123 and 1-1441, andone compound selected from the group consisting of mecoprop, fluroxypyrand ioxynil at a weight ratio of 1:0.5 to 50.

[0718] 6. A mixture of one compound selected from the group consistingof compounds 1-439, 1-482, 1-486, 1-496, 1-1076, 1-1123 and 1-1441, andone compound selected from the group consisting of diflufenican,metsulfuron-methyl, fenoxaprop-ethyl and clodinafop-propargyl at aweight ratio of 1:0.1 to 10.

[0719] 7. A mixture of one compound selected from the group consistingof compounds 1-1141, 1-1222 and 2-203, and one compound selected fromthe group consisting of glyphosate, glufosinate-ammonium and paraquat ata weight ratio of 1:1 to 100.

[0720] Moreover, the present compounds may also be used in admixturewith insecticides, acaricides, nematocides, fungicides, plant growthregulators, fertilizers, soil improver, and the like.

[0721] When the present compounds are used as active ingredients ofherbicides, the application amount is usually in the range of 0.01 to10,000 g, preferably 1 to 8000 g, per hectare, although it may varydepending upon the weather conditions, formulation type, applicationtiming, application method, soil conditions, crop plants, unfavorableweeds, and the like. In the case of emulsifiable concentrates, wettablepowders, flowables, concentrated emulsions, water-dispersible granules,or the like, the formulation is usually applied at a prescribed amountafter diluted with water having a volume of about 10 to 1000 liters perhectare, if necessary, with the addition of an adjuvant such as aspreading agent. In the case of granules or some types of flowables, theformulation is usually applied as such without any dilution.

[0722] Examples of the adjuvant used, if necessary, may include, inaddition to the surfactants recited above, polyoxyethylene resin acids(esters), ligninsulfonates, abietates, dinaphthylmethanedisulfonates,crop oil concentrates, and vegetable oils such as soybean oil, corn oil,cotton seed oil, and sunflower oil.

[0723] The present compounds can also be used as active ingredients ofharvesting aids such as defoliants and desiccating agents for cotton,and desiccating agents for potato. In these cases, the present compoundsare usually formulated in the same manner as the case where they areused as active ingredients of herbicides, and used alone or incombination with other harvesting aids for foliar treatment before theharvesting of crops.

[0724] The present invention will be further illustrated by thefollowing production examples, reference examples, formulation examples,and test examples; however, the present invention is not limited tothese examples.

[0725] The following will describe production examples for the presentcompounds and the hydrazones of formula [2] as the intermediatecompounds, where the present compounds are designated by their compoundnumbers shown in Tables 1 to 5.

PRODUCTION EXAMPLE 1 Production of Compound 2-631

[0726] To a mixed solution of 8.0 g (97.2 mmol) of sodium acetate and 50ml of water was added under ice cooling 6.6 g (24.3 mmol) of1,1-dibromo-3,3,3-trifluoroacetone, and the reaction was allowed toproceed at 80° C. for 30 minutes. Then, the reaction mixture was cooledto 0° C., to which 4.4 g (18.7 mmol) of7-fluoro-6-hydrazino-4-propargyl-2H-1,4-benzoxazin-3-one was added, andthe reaction mixture was stirred at room temperature for 2 hours. Theprecipitated crystals were collected by filtration, washed twice with 10ml of water, and dried, which afforded 6.3 g (18.37 mmol) of7-fluoro-6-trifluoroacetylmethylidenhydrazino-4-propargyl-2H-1,4-benzoxazin-3-one[another name: 3,3,3-trifluoro-2-oxopropanal1-(7-fluoro-3-oxo-4-propargyl-2H-1,4-benzoxazin-6-ylhydrazone)], m.p.190.6° C. (decomp.).

[0727] To a mixed solution of 6.0 g (17.5 mmol) of the above compoundand 50 ml of toluene was added 9.1 g (26.2 mmol) ofcarbethoxymethylenetriphenylphosphorane, and the mixture was heatedunder reflux for 1 hour. The toluene was distilled out under reducedpressure, and the residue was subjected to silica gel columnchromatography, which afforded 1.3 g (3.5 mmol) of7-fluoro-6-[5-trifluoromethyl-3-pyridazinon-2-yl]-4-propargyl-2H-1,4-benzoxazin-3-one(compound 2-631).

PRODUCTION EXAMPLE 2 Production of Compound 1-476

[0728] To a mixed solution of 5.3 g (53.5 mmol) of sodium acetate andabout 100 ml of water was added under ice cooling 6.6 g (24.3 mmol) of1,1-dibromo-3,3,3-tri-fluoroacetone, and the reaction was allowed toproceed at 70° C. for 20 minutes. Then, the reaction mixture was cooledto room temperature, to which a solution of 5.8 g (21.5 mmol) of2-fluoro-4-chloro-5-isopropoxyphenylhydrazine dissolved in about 20 mlof diethyl ether was added, and the reaction mixture was stirred at roomtemperature for 1 hour. The ether layer was separated and concentrated.Then, about 60 ml of THF was added to the residue, to which 8.3 g (23.0mmol) of carbethoxyethylidene-triphenylphosphorane was added, and themixture was heated under reflux for 2 hours. The toluene was distilledout under reduced pressure, and the residue was subjected to silica gelcolumn chromatography, which afforded 3.8 g (10.5 mmol) of2-[2-fluoro-4-chloro-5-isopropoxyphenyl]-4-methyl-5-trifluoromethylpyridazin-3-one(compound 1-476)

PRODUCTION EXAMPLE 3 Production of Compound 1-391

[0729] First, 3.5 g (9.7 mmol) of2-[2-fluoro-4-chloro-5-isopropoxyphenyl]-4-methyl-5-trifluoromethylpyridazin-3-one(compound 1-476) was dissolved in about 10 ml of concentrated sulfuricacid under ice cooling, and the solution was warmed to room temperature.After 10 minutes, about 100 ml of water was added to the reactionmixture, and the precipitated crystals were collected by filtration, andwashed twice with 20 ml of water and once with 10 ml of hexane. Thesecrystals were recrystallized from isopropanol, which afforded 3.2 g (9.0mmol) of2-[2-fluoro-4-chloro-5-hydroxyphenyl]-4-methyl-5-trifluoromethylpyridazin-3-one(compound 1-391).

PRODUCTION EXAMPLE 4 Production of Compound 1-486

[0730] First, 3.2 g (10 mmol) of compound 1-391 was dissolved in about50 ml of DMF, to which 2.0 g (13 mmol) of potassium carbonate was addedat room temperature and 1.3 g (11 mmol) of propargyl bromide was thenadded, and the mixture was stirred at room temperature for 30 minutes,followed by the addition of 100 ml of water. The precipitated crystalswere collected by filtration, washed with hexane, and recrystallizedfrom isopropanol, which afforded 3.4 g (9 mmol) of compound 1-486.

PRODUCTION EXAMPLE 5 Production of Compound 1-496

[0731] First, 3.2 g (10 mmol) of compound 1-391 was dissolved in about50 ml of DMF, to which 0.44 g (11 mmol) of sodium hydride (60 wt. %, oildispersion) was added, and the mixture was allowed to stand at roomtemperature for 30 minutes, followed by the addition of 1.8 g (11 mmol)of ethyl bromoacetate under ice cooling. After stirring at roomtemperature for 1 hour, the reaction mixture was extracted with diethylether. The organic layer was washed with 10% aqueous HCl, aqueous sodiumbicarbonate solution and then with saturated sodium chloride solution,and dried with anhydrous magnesium sulfate. The solvent was distilledout under reduced pressure, and the residue was subjected to silica gelcolumn chromatography, which afforded 2.4 g (5.5 mmol) of compound1-496.

PRODUCTION EXAMPLE 6 Production of Compound 2-251

[0732] To a mixed solution of 5.3 g (53.5 mmol) of sodium acetate andabout 50 ml of water was added under ice cooling 6.6 g (24.3 mmol) of1,1-dibromo-3,3,3-trifluoro-acetone, and the reaction was allowed toproceed at 80° C. for 1 hour. Then, the reaction mixture was cooled to0° C., to which 4.4 g (18.7 mmol) of7-fluoro-6-hydrazino-4-propargyl-2H-1,4-benzoxazin-3-one was added, andthe reaction mixture was stirred at room temperature for 2 hours. Theprecipitated crystals were collected by filtration, washed twice with 10ml of water and once with 10 ml of hexane, and then dissolved in 50 mlof toluene without drying. To this solution was added 8.8 g (24.3 mmol)of carbethoxyethylidenetriphenylphosphorane, and the mixture was heatedunder reflux for 1 hour, while conducting azeotropic dehydration. Thetoluene was distilled out under reduced pressure, and the residue wassubjected to silica gel column chromatography, which afforded 3.5 g(9.01 mmol) of compound 2-251.

Production Example 7 Production of Compound 2-328

[0733] To a mixed solution of 5.3 g (53.5 mmol) of sodium acetate andabout 50 ml of water was added under ice cooling 6.6 g (24.3 mmol) of1,1-dibromo-3,3,3-trifluoroacetone, and the reaction was allowed toproceed at 80° C. for 1 hour. Then, the reaction mixture was cooled to0° C., to which 4.8 g (I 8.7 mmol) of6-fluoro-5-hydrazino-3-(secbutyl)-1,3-benzothiazol-2-one was added, andthe reaction mixture was stirred at room temperature for 2 hours. Then,100 ml of ether was added to the reaction mixture, followed by stirringand phase separation, and the organic layer was concentrated. Theresidue was dissolved in 50 ml of THF, to which 8.8 g (24.3 mmol) ofcarbethoxyethylidenetriphenylphosphorane was added, and the mixture washeated under reflux for 1 hour. The THF was distilled out under reducedpressure, and the residue was subjected to silica gel columnchromatography, which afforded 3.7 g (9.6 mmol) of compound 2-328.

PRODUCTION EXAMPLE 8 Production of Compound 1-347

[0734] First, 50 ml of concentrated sulfuric acid was ice cooled, inwhich 7.0 g (22.8 mmol) of compound 1-341 was dissolved. Then, 1.51 g(24 mmol) of fuming nitric acid was added dropwise at 5° C. or lower,followed by maturation at 0° to 5° C. for 1 hour. The mixture was pouredinto 300 ml of ice-water and extracted three times with 50 ml of ether.The combined ether layer was washed with about 100 ml of water andneutralized with 100 ml of aqueous sodium bicarbonate solution, followedby phase separation. The organic layer was dried with magnesium sulfateand concentrated to half volume, and the residue was subjected to silicagel column chromatography, which afforded 6.1 g (17.4 mmol) of compound1-347.

PRODUCTION EXAMPLE 9 Production of Compound 1-353

[0735] First, 5.0 g of iron powder, 75 ml of acetic acid, and 10 ml ofwater were mixed, and the mixture was warmed to about 80° C., followedby maturation for about 15 minutes. Then, 6.0 g (17.1 mmol) of compound1-347 was dissolved in 40 ml of ethyl acetate, which was added dropwiseto the above mixture at 80° C. or lower. After maturation at about 80°C. for 1 hour, the reaction mixture was allowed to stand for cooling toroom temperature, and extracted twice with 100 ml of ethyl acetate. Thecombined ethyl acetate layer was washed twice with 50 ml of water andneutralized with aqueous sodium bicarbonate solution, followed by phaseseparation. The organic layer was dried with magnesium sulfate, and theethyl acetate was distilled out under reduced pressure. The residue wassubjected to silica gel chromatography, which afforded 5.1 g (15.9 mmol)of compound 1-353.

PRODUCTION EXAMPLE 10 Production of Compound 1-420

[0736] First, 500 mg (1.6 mmol) of compound 1-353 was mixed with 10 ml(77.3 mmol) of ethyl 2-bromopropionate, and the mixture was heated underreflux at about 160° C. for about 12 hours. After allowing to stand forcooling, the reaction mixture was subjected to silica gel columnchromatography, which afforded 60 mg (0.6 mmol) of compound 1-420.

PRODUCTION EXAMPLE 11 Production of Compound 1-1622

[0737] First, 6 ml (55.4 mmol) of ethyl acrylate, 0.5 g (4.8 mmol) oft-butyl nitrite, and 0.6 g (4.5 mmol) of copper (II) chloride were mixedtogether in 5 ml of acetonitrile, followed by ice cooling. Then, 1.0 g(3.1 mmol) of compound 1-353 dissolved in 5 ml of acetonitrile was addeddropwise at 5° C. or lower, followed by overnight maturation at roomtemperature. The reaction mixture was poured into ice-water andextracted twice with 100 ml of ethyl acetate. The combined ethyl acetatelayer was washed with 50 ml of diluted hydrochloric acid and dried withmagnesium sulfate. The solvent was distilled out under reduced pressure,and the residue was subjected to silica gel column chromatography, whichafforded 0.51 g (1.2 mmol) of compound 1-1622.

PRODUCTION EXAMPLE 12 Production of Compound 1-1221

[0738] To a mixed solution of 5.3 g (53.5 mmol) of sodium acetate andabout 50 ml of water was added under ice cooling 6.6 g (24.3 mmol) of1,1-dibromo-3,3,3-trifluoro-acetone, and the reaction was allowed toproceed at 80° C. for 1 hour. Then, the reaction mixture was cooled to0° C., to which 5.2 g (18.7 mmol) of methyl2-(2-chloro-4-fluoro-5-hydrazinophenylthio)propionate was added, and thereaction mixture was stirred at room temperature for 2 hours. Theprecipitated crystals were collected by filtration, washed twice with 10ml of water and once with 10 ml of hexane, and dried. The residue wasdissolved in 50 ml of THF, to which 8.4 g (22.4 mmol) ofcarbethoxymethylenetriphenylphosphorane was added, and the solution wasstined at room temperature for 3 hours. The THF was distilled out underreduced pressure, and the residue was subjected to silica gel columnchromatography, which afforded 3.8 g (9.0 mmol) of compound 1-1221.

PRODUCTION EXAMPLE 13 Production of Compound 2-821

[0739] To a mixed solution of 8.0 g (97.2 mmol) of sodium acetate andabout 50 ml of water was added under ice cooling 6.9 g (24.3 mmol) of3,3-dibromo-1,1,1-trifluorobutanone, and the reaction was allowed toproceed at 80° C. for 30 minutes. Then, the reaction mixture was cooledto 0° C., to which 4.4 g (18.7 mmol) of7-fluoro-6-hydrazino-4-propargyl-2H-1,4-benzoxazin-3-one was added, andthe reaction mixture was stirred at room temperature for 2 hours. Theprecipitated crystals were collected by filtration, washed twice with 10ml of water, and dried, which afforded 6.1 g (17.0 mmol) of1,1,1-trifluoro-2,3-butandione3-(7-fluoro-3-oxo-4-propargyl-2H-1,4-benzoxazin-6-ylhydrazone).

[0740] To a mixed solution of 6.1 g (17.0 mmol) of the above compoundand 50 ml of THF was added 7.1 g (20.4 mmol) ofcarbethoxymethylenetriphenylphosphorane, and the mixture was heatedunder reflux for 1 hour. The THF was distilled out under reducedpressure, and the residue was subjected to silica gel columnchromatography, which afforded 0.61 g (1.6 mmol) of7-fluoro-6-(6-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one(compound 2-821).

REFERENCE EXAMPLE 1

[0741] This is a production example for 3,3-dibromo-1,I,1-trifluoro-2-butanone used in Production Example 13.

[0742] First, 34.0 g of sodium acetate was dissolved in 270 ml of aceticacid, to which 25 g (0.20 mol) of 1,1,1-trifluoro-2-butanone was added,and while keeping the temperature at 15° to 20° C., 66.3 g (0.42 mol) ofbromine was added dropwise over 45 minutes. The reaction mixture wasstirred for 5 hours, while keeping the temperature at 15° to 20° C., andthen allowed to stand at room temperature for 68 hours. The supernatantwas taken and washed with 600 ml of concentrated sulfuric acid. Furtherwashing with 307 ml of concentrated sulfuric acid and distillation undernormal pressure gave 28 g (0.10 mol) of3,3-dibromo-1,1,1-trifluoro-2-butanone.

PRODUCTION EXAMPLE 14 Production of Compound 1-1 346

[0743] To a mixed solution of 5.3 g (53.5 mmol) of sodium acetate andabout 50 ml of water was added under ice cooling, 6.9 g (243 mmol) of3,3-dibromo-1,1,1-trifluoro-2-butanone, and the reaction was allowed toproceed at 80° C. for 1 hour. Then, the reaction mixture was cooled to0° C., to which 3.3 g (18.7 mmol) of 2-chloro-4-fluoro-5-hydrazinophenolwas added, and the reaction mixture was stirred at room temperature for2 hours. The precipitated crystals were collected by filtration, washedtwice with 10 ml of water and once with 10 ml of hexane, dried, and thendissolved in 50 ml of THF. To this solution was added 8.8 g (24.3 mmol)of carbethoxymethylenetriphenylphosphorane, and the mixture was stirredat room temperature for 3 hours. The THF was distilled out under reducedpressure, and the residue was subjected to silica gel chromatography,which afforded 0.51 g (1.6 mmol) of compound 1-1346.

PRODUCTION EXAMPLE 15 Production of Compound 1-1441

[0744] First, 3.2 g (10 mmol) of compound 1-1346 was dissolved in about50 ml of DMF, to which 2.0 g (13 mmol) of potassium carbonate was addedat room temperature and 1.3 g (11 mmol) of propargyl bromide was thenadded, and the mixture was stirred at room temperature for 30 minutes,followed by the addition of 100 ml of water. The precipitated crystalswere collected by filtration, washed with hexane, and recrystallizedfrom isopropanol, which afforded 3.2 g (8.5 mmol) of compound 1-1441.

PRODUCTION EXAMPLE 16 Production of Compound 1-499

[0745] This example followed the procedures of Production Example 5,except that 1.8 g (1.1 mmol) of n-pentyl chloroacetate was used in placeof ethyl bromoacetate. After the addition of this compound, the reactionmixture was stirred at 40° C. for 3 hours and then extracted withdiethyl ether. The organic layer was washed with 10% HCl, aqueous sodiumbicarbonate solution and saturated sodium chloride solution, and driedwith anhydrous magnesium sulfate. The solvent was distilled out underreduced pressure, and the residue was subjected to silica gelchromatography, which afforded 3.8 g (8.0 mmol) of compound 1-499.

PRODUCTION EXAMPLE 17 Production of Compound 2-203

[0746] To a mixed solution of 5.3 g (53.5 mmol) of sodium acetate andabout 50 ml of water was added under ice cooling 6.6 g (24.3 mmol) of1,1-dibromo-3,3,3-trifluoroacetone, and the reaction was allowed toproceed at 80° C. for 1 hour. Then, the reaction mixture was cooled to0° C., to which 4.0 g (18.7 mmol) of6-hydrazino-4-propargyl-2H-1,4-benzoxazin-3-one was added, and thereaction mixture was stirred at room temperature for 2 hours. Theprecipitated crystals were collected by filtration, washed twice with 10ml of water and once with 10 ml of hexane, and then dissolved in 50 mlof THF without drying. To this solution was added 8.8 g (24.3 mmol) ofcarbethoxyethylidenetriphenylphosphorane, and the mixture was heatedunder reflux for 3 hours. The THF was distilled out under reducedpressure, and the residue was subjected to silica gel columnchromatography, which afforded 3.3 g (8.8 mmol) of compound 2-203.

PRODUCTION EXAMPLE 18 Production of Compound 1-1222

[0747] To a mixed solution of 5.3 g (53.5 mmol) of sodium acetate andabout 50 ml of water was added under ice cooling 6.6 g (24.3 mmol) of1,1-dibromo-3,3,3-trifluoroacetone, and the reaction was allowed toproceed at 80° C. for 1 hour. Then, the reaction mixture was cooled to0° C., to which 5.5 g (18.7 mmol) of ethyl2-(2-chloro-4-fluoro-5-hydrazinophenylthio)propionate was added, and thereaction mixture was stirred at room temperature for 2 hours. Theprecipitated crystals were collected by filtration, washed twice with 10ml of water and once with 10 ml of hexane, dried, and then dissolved in50 ml of THF. To this solution was added 8.4 g (22.4 mmol) ofcarbethoxymethylenetriphenylphosphorane, and the mixture was stirred atroom temperature for 3 hours. The THF was distilled out under reducedpressure, and the residue was subjected to silica gel columnchromatography, which afforded 4.3 g (9.9 mmol) of compound 1-1222.

PRODUCTION EXAMPLE 19 Production of Compound 1-476

[0748] To a mixed solution of 5.3 g (53.5 mmol) of sodium acetate andabout 100 ml of water was added under ice cooling 6.6 g (24.3 mmol) of1,1-dibromo-3,3,3-trifluoroacetone, and the reaction was allowed toproceed at 70° C. for 20 minutes. Then, the reaction mixture was cooledto room temperature, to which a solution of 5.8 g (21.5 mmol) of2-fluoro-4-chloro-5-isopropoxyphenylhydrazine dissolved in about 20 mlof diethyl ether was added, and the reaction mixture was stirred at roomtemperature for 1 hour. The ether layer was separated, washed once with10 ml of saturated sodium chloride solution, and dried with magnesiumsulfate. The diethyl ether was distilled out, which afforded 6.5 g (20.0mmol) of 3,3,3-trifluoro-2-oxo-propanal1-(4-chloro-2-fluoro-5-isopropoxyphenylhydrazone).

[0749]¹H-NMR (250 MHz, CDCl₃, TMS δ (ppm)) 1.39 (6H, d, J=6.0 Hz),4.38-4.52 (1H, m), 7.15 (1H, d, J=10.5 Hz), 7.22 (1H, d, J=7.3 Hz), 7.43(1H, q, J=1.7 Hz), 9.18 (1H, br).

[0750] This compound was dissolved in 50 ml of THF. To this solution wasadded 8.3 g (23.0 mmol) of carbethoxyethylidenetriphenylphosphorane, andthe mixture was heated under reflux for 2 hours. The THF was distilledout under reduced pressure, and the residue was subjected to silica gelcolumn chromatography, which afforded 3.8 g (10.5 mmol) of2-[2-fluoro-4-chloro-5-isopropoxyphenyl]-4-methyl-5-trifluoromethylpyridazin-3-one(compound 1-476).

PRODUCTION EXAMPLE 20 Production of Compound 1-642

[0751] To a mixed aqueous solution of 5.3 g (53.5 mmol) of sodiumacetate and about 100 ml of water was added under ice cooling 6.6 g(24.3 mmol) of 1,1-dibromo-3,3,3-trifluoroacetone, and the reaction wasallowed to proceed at 70° C. for 20 minutes. Then, the reaction mixturewas cooled to room temperature. Separately, 5.8 g (21.5 mmol) of crudeethyl 2-chloro-4-fluoro-5-hydrazinobenzoate hydrochloride was dissolvedin 30 ml of water, to which 100 ml of diethyl ether was added, and whilecooling, the mixture was neutralized by the addition of saturated sodiumhydrogencarbonate solution, followed by washing with saturated sodiumchloride solution, which afforded a solution of ethyl2-chloro-4-fluoro-5-hydrazinobenzoate in diethyl ether. This solutionwas added to the above reaction mixture, followed by vigorous stirringat room temperature for 2 hours. The ether layer was separated, washedonce with 10 ml of saturated sodium chloride solution, and dried withmagnesium sulfate. The diethyl ether was distilled out. The residue wasdissolved in 50 ml of THF, to which 8.3 g (23.0 mmol) ofcarbethoxyethylidenetriphenylphosphorane was added, and the mixture washeated under reflux for 2 hours. The THF was distilled out under reducedpressure, and the residue was subjected to silica gel columnchromatography, which afforded 3.8 g (10.0 mmol) of compound 1-642.

REFERENCE EXAMPLE 2

[0752] This is a production example for ethyl2-chloro-4-fluoro-5-hydrazinobenzoate hydrochloride used in ProductionExample 20.

[0753] First, 50 g (0.29 mol) of 2-chloro-4-fluorobenzoic acid wasdissolved in 150 ml of hydrochloric acid at room temperature, to which amixed acid of 28 ml (0.31 mol) of fuming nitric acid and 56 ml ofconcentrated sulfuric acid was added dropwise at 35° to 45° C. Then, thesolution was stirred at 40° C. for 1 hour and poured into 250 ml ofice-water. The precipitated crystals were collected by filtration andrecrystallized from a mixed solution of hexane and ethyl acetate, whichafforded 55 g (0.25 mol) of 2-chloro-4-fluoro-5-nitrobenzoic acid. Then,55 g (0.25 mol) of 2-chloro-4-fluoro-5-nitrobenzoic acid was dissolvedin 50 ml of ethyl acetate, to which 33 g (0.28 mol) of thionyl chloridewas added, and the mixture was heated under reflux for 3 hours and thenallowed to stand for cooling to room temperature. Then, 20 ml of ethanoland 30 g of triethylamine were added under ice cooling, and the mixturewas stirred at room temperature for 2 hours. The solvent was distilledout, and the residue was purified by silica gel chromatography, whichafforded 57 g (0.23 mol) of ethyl 2-chloro-4-fluoro-5-nitrobenzoate.

[0754] Then, 60 g of iron powder and 500 ml of 10% acetic acid weremixed, and the mixture was heated to 40° C. Separately, 50 g (0.20 mol)of ethyl 2-chloro-4-fluoro-5-nitrobenzoate was dissolved in a mixedsolution of 20 ml of acetic acid and 20 ml of ethyl acetate, and addeddropwise to the above iron powder-acetic acid mixed solution. Then, thereaction mixture was stirred at 50° C. for 1 hour and filtered thoughcelite. The filtrate was extracted with 100 ml of ethyl acetate. Theethyl acetate layer was washed with aqueous sodium bicarbonate solutionand saturated sodium chloride solution, and dried with magnesiumsulfate. The solvent was distilled out, and the residue was purified bysilica gel chromatography, which afforded to 40 g (0.18 mol) of ethyl5-amino-2-chloro-4-fluorobenzoate.

[0755] Then, 19 g (87.4 mmol) of ethyl 5-amino-2-chloro-4-fluorobenzoatewas dissolved in 120 ml of hydrochloric acid, followed by cooling to 0°C., to which a solution of 6.3 g (91.7 mmol) of sodium nitrite dissolvedin 10 ml of water was added dropwise at 10° C. or lower. The mixture wasstirred at 0° C. for 30 minutes and then cooled to −30° C., into which asolution of 58 g (0.31 mol) of anhydrous tin (11) chloride dissolved in40 ml of hydrochloric acid was poured, followed by further stirring at0° C. for 3 hours. The precipitated crystals were collected byfiltration and then dried, which afforded 13.6 g (50.7 mmol) of crudeethyl 2-chloro-4-fluoro-5-hydrazinobenzoate hydrochloride.

PRODUCTION EXAMPLE 21 Production of Compound 1-1789

[0756] First, 5.0 g (15.5 mmol) of compound 1-391 was dissolved in about50 ml of DMF, to which 2.8 g (20.2 mmol) of potassium carbonate wasadded at room temperature and then 1.5 g (17.1 mmol) of3-bromo-2-methyl-1-propene was added, and the mixture was stirred atroom temperature for 30 minutes, followed by the addition of 100 ml ofwater. The precipitated crystals were collected by filtration, washedwith hexane, and recrystallized from isopropanol, which afforded 4.4 g(13.2 mmol) of compound 1-1789.

PRODUCTION EXAMPLE 22 Production of Compound 4-451

[0757] First, 4.0 g (12.0 mmol) of compound 1-1789 was dissolved in 20ml of N,N-dimethylaniline, and the solution was heated at 180° C. for 3hours. After cooling to room temperature, 100 ml of ethyl acetate wasadded, and the mixture was washed with 1N aqueous hydrochloric acid andsaturated sodium chloride solution, and dried with magnesium sulfate.The solvent was distilled out, and the precipitated crystals wererecrystallized from isopropanol, which afforded 3.4 g (10.2 mmol) of2-[4-chloro-6-fluoro-3-hydroxy-2-(2-methyl-2-propenyl)]-4-methyl-5-trifluoromethylpyridazin-3-one,m.p. 133.2° C.

[0758] The product was dissolved in 30 ml of xylene, to which acatalytic amount of p-toluenesulfonic acid was added, and the mixturewas heated under reflux for 1 hour. After cooling to room temperature,100 ml of ethyl acetate was added, and the mixture was washed withaqueous sodium bicarbonate solution and sodium chloride solution, anddried with magnesium sulfate. The solvent was distilled out, and theresidue was purified by silica gel column chromatography, which afforded3.0 g (9.0 mmol) of compound 4-451.

PRODUCTION EXAMPLE 23 Production of Compound 1-483

[0759] First, 5.0 g (15.5 mmol) of compound 1-391 was dissolved in about20 ml of DMF, to which 2.4 g (17.1 mmol) of potassium carbonate wasadded at room temperature. The solution was heated to about 40° C., towhich 1.7 g (17.1 mmol) of 2,3-dichloropropene was added, and after 1hour, the mixture was allowed to stand for cooling and poured intoice-water. The precipitated crystals were collected by filtration,washed with hexane, and recrystallized from isopropanol, which afforded5.2 g (13.1 mmol) of compound 1-483.

PRODUCTION EXAMPLE 24 Production of Compound 3-139

[0760] First, 3.0 g (7.6 mmol) of compound 1-436 was dissolved in 10 mlof N,N-dimethylaniline, and the solution was heated under reflux for 3hours. After cooling to room temperature, 50 ml of ethyl acetate wasadded, and the mixture was washed with 1N aqueous hydrochloric acid andsaturated sodium chloride solution, and dried with magnesium sulfate.The solvent was distilled out, and the precipitated crystals wererecrystallized from isopropanol, which afforded 2.2 g (5.6 mmol) of2-[4-chloro-6-fluoro-3-hydroxy-2-(2-chloro-2-propenyl)]-4methyl-5-trifluoromethylpyridazin-3-one.

[0761]¹H-NMR (300 MHz, CDCl₃, TMS δ (ppm)) 2.41 (3H, q, J═1.9 Hz), 3.56(1H, d, J═16.3 Hz), 3.72 (1H, d, J═16.3 Hz), 4.91 (1H, q, J=1.4 Hz),5.12 (1H, d, J═1.5 Hz), 5.72 (1H, s), 7.25 (1H, d, J═8.7 Hz), 8.00 (1H,s)

[0762] The product was dissolved in 10 ml of trifluoromethanesulfonicacid cooled by ice, and the solution was stirred under ice cooling.After 30 minutes, the solution was poured into ice-water, and theprecipitated crystals were collected by filtration and subjected tosilica gel column chromatography, which afforded 1.9 g (5.4 mmol) ofcompound 3-139.

PRODUCTION EXAMPLE 25 Production of Compound 1-1744

[0763] This example followed the procedures of Production Example 20,except that 6.1 g (21.5 mmol) of ethyl 2,4-dichloro-5-hydrazinobenzoatehydrochloride was used in place of ethyl2-chloro-4-fluoro-5-hydrazinobenzoate hydrochloride, which afforded 4.8g (12.2 mmol) of compound 1-1744.

[0764] The ethyl 2,4-dichloro-5-hydrazinobenzoate hydrochloride usedabove was produced from 2,4-dichlorobenzoic acid by the same process asshown in Reference Example 2.

PRODUCTION EXAMPLE 26 Production of Compound 1-1279

[0765] To a mixed aqueous solution of 5.3 g (53.5 mmol) of sodiumacetate and about 100 ml of water was added under ice cooling 6.6 g(24.3 mmol) of 1,1-dibromo-3,3,3-trifluoroacetone, and the reaction wasallowed to proceed at 70° C. for 20 minutes. Then, the reaction mixturewas cooled to room temperature. Separately, 5.8 g (21.5 mmol) of ethyl2-chloro-4-fluoro-5-hydrazinobenzoate hydrochloride was dissolved in 30ml of water, to which 100 ml of diethyl ether was added, and whilecooling, the mixture was neutralized by the addition of saturated sodiumhydrogencarbonate solution, followed by washing with saturated sodiumchloride solution, which afforded a solution of ethyl2-chloro-4-fluoro-5-hydrazinobenzoate in diethyl ether. This solutionwas added to the above reaction mixture, followed by vigorous stirringat room temperature for 2 hours. The ether layer was separated, washedonce with 10 ml of saturated sodium chloride solution, and dried withmagnesium sulfate. The diethyl ether was distilled out, and a smallamount of hexane was added to give 4.3 g (12.6 mmol) of ethyl2-chloro-4-fluoro-5-(2-oxo-3,3,3-trifluoropentylidenehydrazino)benzoate.This product was dissolved in 50 ml of THF, to which 5.0 g (14.4 mmol)of carbethoxymethylenetriphenylphosphorane was added, and the mixturewas heated under reflux for 2 hours. The THF was distilled out underreduced pressure, and the residue was subjected to silica gel columnchromatography, which afforded 3.6 g (9.7 mmol) of compound 1-1279.

PRODUCTION EXAMPLE 27 Production of Compound 1-1780

[0766] First, 50 g (0.61 mol) of sodium acetate and 41 g (0.14 mol) of1,1-dibromo-3,3,3-trifluoroacetone were mixed with 500 ml of water, andthe mixture was stirred at 80° C. for 30 minutes and then cooled to 0°C. Then, 45 g (0.14 mol) of 4-bromo-2-fluoro-5-isopropoxyphenylhydrazinehydrochloride was added at 10° C. or lower, and the mixture was stirredat 10° C. or lower for 3 hours. The precipitated crystals were collectedby filtration and dried, which afforded 35 g (94.3 mmol) of3,3,3-trifluoro-2-oxopropanal1-(4-bromo-2-fluoro-5-isopropoxyphenylhydrazone).

[0767] Then, 16 g (46.0 mmol) of carbethoxymethylenetriphenylphosphoraneand 16 g (43.1 mmol) of 3,3,3-trifluoro-2-oxopropanal1-(4-bromo-2-fluoro-5-isopropyloxyphenylhydrazone) were stirred in 100ml of THF at room temperature for 4 hours. After completion of thereaction, the reaction mixture was concentrated, and the residue wassubjected to silica gel chromatography, which afforded 9.4 g (23.8 mmol)of compound 1-1780.

REFERENCE EXAMPLE 3

[0768] This is a production example for4-bromo-2-fluoro-5-isopropoxyphenylhydrazine hydrochloride used inProduction Example 27.

[0769] First, 93 g (0.49 mol) of 2-bromo-4-fluorophenol was suspended in200 ml of water, into which 55 g (0.59 mol) of methyl chloroformate anda solution of 21.5 g (0.51 mol) of sodium hydroxide in 60 ml of waterwere poured together at 10° C. or lower, and the mixture was stirred atthe same temperature for 2 hours. The precipitated crystals werecollected by filtration, washed with water, and dried in a vacuum oven,which afforded 111.6 g (0.45 mol) of methyl2-bromo-4-fluorophenoxyformate.

[0770] Then, 110 g (0.44 mol) of methyl 2-bromo-4-fluorophenoxyformatewas dissolved in 250 ml of sulfuric acid, to which a mixed acid of 30 gof fuming nitric acid and 30 ml of sulfuric acid was added dropwise at5° C. or lower, and the mixture was stirred for 2 hours. The reactionmixture was poured onto ice, and the precipitated crystals werecollected by filtration, washed with water, and dried, which afforded126 g (0.43 mol) of methyl 2-bromo-4-fluoro-5-nitrophenoxyformate.

[0771] Then, 125 g (0.43 mol) of methyl2-bromo-4-fluoro-5-nitrophenoxyformate was suspended in 200 ml of water,to which 19 g (0.47 mol) of sodium hydroxide was added, and the mixturewas stirred at 50° to 60° C. for 4 hours. After completion of thereaction, the reaction mixture was cooled to room temperature and washedwith chloroform. The aqueous layer was acidified with aqueoushydrochloric acid and extracted with ethyl acetate. The ethyl acetatelayer was dried and concentrated, which afforded 104 g (0.43 mol) of2-bromo-4-fluoro-5-nitrophenol.

[0772] Then, 100 g (0.42 mol) of 2-bromo-4-fluoro-5-nitrophenol wasdissolved in 400 ml of dimethylformamide, to which 70 g (0.50 mol) ofpotassium carbonate was added and after warming to 50° C., 94 g (0.55mol) of isopropyl iodide was added dropwise, and the mixture was stirredat 45° to 50° C. for 1 hour. After completion of the reaction, thereaction mixture was poured into water and extracted with ethyl acetate.The ethyl acetate layer was washed with water and then with dilutedhydrochloric acid, dried, and concentrated. The residue was subjected tocolumn chromatography, which afforded 99.8 g (0.36 mol) of2-bromo-4-fluoro-5-nitrophenyl isopropyl ether.

[0773] Then, 60 g (0.22 mol) of 2-bromo-4-fluoro-5-nitrophenyl isopropylether was dissolved in 300 ml of ethyl acetate, to which 1.0 g of 10%palladium-carbon was added, and the hydrogenation was effected under anatmosphere of hydrogen. After completion of the reaction, thepalladium-carbon was removed by filtration, and the filtrate wasconcentrated, which afforded 52 g (0.21 mol) of4-bromo-2-fluoro-5-isopropoxyaniline.

[0774] Then, 108 g (0.57 mol) of tin (11) chloride was dissolved in 100ml of concentrated hydrochloric acid, followed by cooling to −30° C., towhich a diazonium solution prepared from 47 g (0.19 mol) of4-bromo-2-fluoro-5-isopropoxyaniline, 13.5 g (0.20 mol) of sodiumnitrite, and 120 ml of hydrochloric acid was added dropwise at 0° C. orlower, and the mixture was stirred at room temperature for 2 hours. Theprecipitated crystals were collected by filtration and dried in a vacuumoven to give 45 g (0.14 mol) of the crude product,4-bromo-2-fluoro-5-isopropoxyphenylhydrazine hydrochloride.

PRODUCTION EXAMPLE 28 Production of Compound 1-1783

[0775] First, 19 g (52.4 mmol) ofcarbethoxyethylidenetriphenylphosphorane and 19 g (63.2 mmol) of3,3,3-trifluoro-2-oxopropanal1-(4-bromo-2-fluoro-5-isopropyloxyphenylhydrazone) were heated underreflux in 100 ml of THF for 5 hours. After completion of the reaction,the reaction mixture was concentrated, and the residue was subjected tosilica gel chromatography, which afforded 9.1 g (22.2 mmol) of compound1-1783.

PRODUCTION EXAMPLE 29 Production of Compound 1-1748

[0776] This example followed the procedures of Production Example 27,except that 41 g (0.41 mol) of 2,4-dichloro-5-isopropoxyphenylhydrazinehydrochloride was used in place of4-bromo-2-fluoro-5-isopropoxyphenylhydrazine hydrochloride, whichafforded 31.3 g (91.3 mmol) of 3,3,3-trifluoro-2-oxopropanal1-(2,4-dichloro-5-isopropoxyphenylhydrazone). Then, this compound and 40g (0.11 mol) of carbethoxyethylidenetriphenylphosphorane were heatedunder reflux in 100 ml of THF for 5 hours. After completion of thereaction, the reaction mixture was concentrated, and the residue wassubjected to silica gel column chromatography, which afforded 21 g (54.8mmol) of compound 1-1748.

[0777] The 2,4-dichloro-5-isopropoxyphenylhydrazine hydrochloride usedabove was produced from 2,4-dichlorophenol by the same process as shownin Reference Example 3.

PRODUCTION EXAMPLE 30 Production of Compound 1-1029

[0778] First, 9 g (22.8 mmol) of2-(4-bromo-2-fluoro-5-isopropyloxyphenyl)-5-trifluoromethylpyridazin-3-onewas added to 50 ml of sulfuric acid, and the mixture was stirred for 1hour. After completion of the reaction, the reaction mixture was pouredonto ice and extracted with ethyl acetate. The ethyl acetate layer wasdried and concentrated, and the residue was subjected to columnchromatography (eluent, hexane:ethyl acetate=5:1), which afforded 5.9 g(16.7 mmol) of compound 1-1029.

PRODUCTION EXAMPLE 31 Production of Compound 1-392

[0779] First, 9 g (22.0 mmol) of2-(4-bromo-2-fluoro-5-isopropyloxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-onewas added to 50 ml of sulfuric acid, and the mixture was stirred for 1hour. After completion of the reaction, the reaction mixture was pouredonto ice and extracted with ethyl acetate. The ethyl acetate layer wasdried and concentrated, and the residue was subjected to columnchromatography (eluent, hexane:ethyl acetate=5:1), which afforded 4.2 g(11.5 mmol) of compound 1-392.

PRODUCTION EXAMPLE 32 Production of Compound 1-1274

[0780] First, 7.4 g (90.2 mmol) of sodium acetate and 8.0 g (28.2 mmol)of 1,1-di-bromo-3,3,3-trifluoroacetone were mixed with 70 ml of water,and the mixture was stirred at 80° C. for 30 minutes and then cooled, towhich 7.0 g of ethyl 2-chloro-5-hydrazinocinnamate was added at 10° C.or lower, and the mixture was stirred for 3 hours. The precipitatedcrystals were collected by filtration and dried, which afforded 9.6 g(27.5 mmol) of ethyl2-chloro-5-(3,3,3-trifluoro-2-oxopropylidenehydrazino)cinnamate.

[0781]¹H-NMR (250 MHz, CDCl₃, TMS δ (ppm)) 1.36 (3H, t, J=6.9 Hz), 4.30(2H, q, J=6.9 Hz), 6.4-6.6 (1H, m), 7.2-7.5 (3H, m), 7.65 (1H, d, J=2.5Hz), 8.0-8.1 (1H, m)

[0782] Then, 1.0 g (2.9 mmol) of carbethoxymethylenetriphenylphosphoraneand 1.0 g (2.9 mmol) of ethyl2-chloro-5-(3,3,3-trifluoro-2-oxopropylidenehydrazino)-cinnamate werestirred in 10 ml of THF at room temperature for 1 hour. After completionof the reaction, the reaction mixture was concentrated, and the residuewas subjected to column chromatography (eluent, hexane:ethylacetate=5:1), which afforded 0.43 g (11.5 mmol) of compound 1-1274.

REFERENCE EXAMPLE 4

[0783] The ethyl 2-chloro-5-hydrazinocinnamate used in ProductionExample 32 was produced by the following process.

[0784] First, 60 g of tin (11) chloride was dissolved in 60 ml ofconcentrated hydrochloric acid, and the mixture was cooled to −30° C.,to which a diazonium solution prepared from 19 g of ethyl5-amino-2-chlorocinnamate and 6.3 g of sodium nitrite was added dropwiseat 0° C. or lower. The reaction mixture was stirred at room temperaturefor 1 hour, and the precipitated crystals were collected by filtration.These crystals were added to ice-water, neutralized with 2N aqueoussodium hydroxide, and extracted with chloroform. The chloroform layerwas dried and concentrated, which afforded 7.0 g of ethyl2-chloro-5-hydrazinocinnanate.

PRODUCTION EXAMPLE 33 Production of Compound 1-637

[0785] First, 1.1 g (2.9 mmol) ofcarbethoxyethylidenetriphenylphosphorane and 1.0 g (2.9 mmol) of ethyl2-chloro-5-(3,3,3-trifluoro-2-oxopropylidenehydrazino)-cinnamate wereheated under reflux in 10 ml of THF for 3 hours. After completion of thereaction, the reaction mixture was concentrated, and the residue wassubjected to column chromatography (eluent, hexane:ethyl acetate=5:1),which afforded 0.66 g (1.7 mmol) of compound 1-637.

PRODUCTION EXAMPLE 34 Production of Compound 1-367

[0786] First, 0.5 g (1.6 mmol) of compound 1-353 was dissolved in 1.5 mlof pyridine, to which 0.2 g (1.7 mmol) of methanesulfonyl chloride wasadded dropwise, followed by stirring for 2 hours. The reaction mixturewas poured into ice-water and extracted with ethyl acetate. The ethylacetate layer was washed with diluted hydrochloric acid, dried, andconcentrated. The residue was subjected to column chromatography(eluent, hexane ethyl acetate=3:1), which afforded 0.42 g (11 mmol) ofcompound 1-367.

PRODUCTION EXAMPLE 35 Production of Compound 1-369

[0787] This example followed the procedures of Production Example 34,except that 0.23 g (1.6 mmol) of chloromethylsulfonyl chloride was usedin place of methanesulfonyl chloride, which afforded 0.38 g (0.91 mmol)of compound 1-369.

PRODUCTION EXAMPLE 36 Production of Compound 1-391

[0788] First, 32.3 g of 3-amino-6-chloro-3-fluorophenol was mixed with150 ml of concentrated hydrochloric acid, and the mixture was stirred at50° C. for 30 minutes, to which a solution of 15 g of sodium nitritedissolved in 40 ml of water was added dropwise at 0° C. over 10 minutes.After stirring at 0° C. for 1 hour, the mixture was cooled to −50° C.Then, a solution of 132 g of tin (11) chloride dissolved in 132 g ofconcentrated sulfuric acid was rapidly added dropwise at −50° C., andthe mixture was gradually warmed to room temperature and stirred for 1hour. The solids formed were collected by filtration and dried at 80° C.under reduced pressure to give 75 g of the crude2-fluoro-4-chloro-5-hydroxyphenylhydrazine hydrochloride crystals.

[0789]¹H-NMR (DMSO-d₆,TMS δ (ppm)) 3-5 (2H, br), 6.73 (1H, d), 7.22 (1H,d), 8.20 (1H, s), 9-11 (2H, br)

[0790] Then, 49.2 g of sodium acetate and 40.5 g of1,1-dibromo-3,3,3-trifluoroacetone were dissolved in 400 ml of water,and the solution was heated at 80° to 90° C. for 40 minutes. Thesolution was cooled to 0° C., to which 75 g of the crude2-fluoro-4-chloro-5-hydroxyphenylhydrazine hydrochloride crystalsobtained above was added, and the mixture was stirred at roomtemperature for 70 minutes. The precipitated crystals were collected byfiltration and dried under reduced pressure, which afforded 35.4 g of3,3,3-trifluoro-2-oxopropanal1-(4-chloro-2-fluoro-5-hydroxyphenylhydrazone).

[0791]¹H-NMR (300 MHz, CDCl₃, TMS δ (ppm)) 5.49 (1H, s), 7.15 (1H, d,J=10.5 Hz), 7.25 (1H, d, J=7.4 Hz), 7.38 (1H, q, J=1.8 Hz), 8.75 (1H, s)

[0792] Then, 12.9 g of 3,3,3-trifluoro-2-oxopropanal1-(4-chloro-2-fluoro-5-hydroxyphenylhydrazone) and 22.3 g ofcarbethoxyethylidenetriphenylphosphorane were dissolved in 110 ml oftetrahydrofuran, and the solution was heated under reflux for 3 hours.The solvent was distilled out under reduced pressure, and the residuewas subjected to silica gel chromatography, which afforded 8.8 g of2-(2-fluoro-4-chloro-5-hydroxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one(compound 1-391).

[0793] The 5-amino-2-chloro-4-fluorophenol used above can be produced bythe method described in the publication of European Patent Application,EP-61741-A.

PRODUCTION EXAMPLE 37 Production of Compound 1-332

[0794] First, 2 g of 3,3,3-trifluoro-2-oxo-1-propanal1-(4-chlorophenylhydrazone) and 2 g of ethyl diethylphosphonoacetatewere mixed with 20 ml of triethylamine, and the reaction was allowed toproceed at 50° C. for 24 hours. The solvent was distilled out underreduced pressure, and the residue was subjected to columnchromatography, which afforded 1.16 g of2-(4-chlorophenyl)-5-trifluoromethylpyridazin-3-one (compound 1-332).

REFERENCE EXAMPLE 5

[0795] The 3,3,3-tri fluoro-2-oxopropanal1-(4-chloro-2-fluoro-5-isopropoxyphenylhydrazone) produced in ProductionExample 19 can also be produced by the following process.

[0796] First, 20.1 g of ethyl 4,4,4-trifluoroacetoacetate and 25 g ofsodium acetate were dissolved in 150 ml of water, to which a diazoniumsolution in hydrochloric acid prepared from 20.3 g of4-chloro-2-fluoro-5-isopropoxyaniline, 20 ml of concentratedhydrochloric acid, 20 ml of water, and 7.35 g of sodium nitrite wasadded dropwise at 11° C. or lower. After stirring at room temperaturefor 1 hour, the precipitated crystals were collected by filtration,washed with water, and dried, which afforded 34 g of the desired productas orange crystals (yield, 85%).

[0797] Then, 15.9 g of the ester obtained above and 1.7 g of lithiumhydroxide monohydrate were added to 30 ml of 1,4-dioxane and 3 ml ofwater, and the mixture was heated under reflux for 6 hours. The reactionmixture was poured into ice-water, neutralized with diluted hydrochloricacid, and extracted with ethyl acetate. The ethyl acetate layer wasdried and concentrated, and the precipitated crystals were washed withhexane, which afforded 1 1.3 g of the desired product as yellow crystals(yield, 76.3%).

[0798] Then, 7.4 g of the calboxylic acid obtained above was dissolvedin 42 ml of N,N-dimethylformamide, and the reaction solution was heatedto 100° C. and kept at the same temperature for 30 minutes. Thereafter,the reaction solution was cooled to room temperature, poured into water,and extracted with ethyl acetate. The ethyl acetate layer was washedwith diluted hydrochloric acid, dried with magnesium sulfate, andconcentrated, which afforded 5.9 g of the desired product as orangecrystals (yield, 90%).

[0799]¹H-NMR (250 MHz, CDCl₃, TMS δ (ppm)) 1.39 (6H, d, J=6.0 Hz),4.38-4.52 (1H, m), 7.15 (1H, d, J=10.5 Hz), 7.22 (1H, d, J=7.3 Hz), 7.43(1H, q, J=1.7 Hz), 9.18 (1H, br)

REFERENCE EXAMPLE 6

[0800] In the same manner as described in Reference Example2,3,3,3-trifluoro-2-oxopropanal 4-chlorophenylhydrazone was produced.

[0801] First, 5.0 g of the ester as the starting material and 0.67 g oflithium hydroxide monohydrate were added to a mixed solution of 30 ml of1,4-dioxane and 2 ml of water, and the mixture was heated under refluxfor 1.5 hours. The reaction mixture was poured into ice-water,neutralized with diluted hydrochloric acid, and extracted with ethylacetate. The ethyl acetate layer was dried with magnesium sulfate andconcentrated, and the precipitated crystals were washed with a mixedsolvent of hexane and diethyl ether (hexane:diethyl ether=2:1), whichafforded 3.3 g of the desired compound as yellow crystals (yield, 73%).

[0802] Process 1) A solution prepared by dissolving 3.3 g of thecarboxylic acid obtained by the above reaction in 10 ml ofdimethylsulfoxide was heated to 100° C. and kept at the same temperaturefor 10 minutes, followed by cooling to room temperature. Thereafter, thereaction mixture was subjected to silica gel chromatography (eluent,hexane:ethyl acetate=7:1), which afforded 2.55 g of the desired product(yield, 91%).

[0803] Process 2) A reaction mixture prepared by adding 5.0 g of thecarboxylic acid obtained by the above reaction, 0.5 ml of quinoline, and0.1 g of copper powder to 40 ml of toluene was heated to 100° C. andkept at the same temperature for 20 minutes. After completion of thereaction, the reaction mixture was cooled to room temperature andsubjected to silica gel chromatography (eluent, hexane:ethylacetate=8:1), which afforded 3.6 g of the desired product (yield, 86%).

[0804] Some of the present compounds are shown with their compoundnumbers in Tables 1 to 5, where the symbol “n” refers to normal-; “i”,iso-; “s”, secondary-; and “c”, cyclo-. TABLE 1 Compounds of theformula:

Compound No. X Y R³ R¹ R² B 1-1 H F H CF₂Cl H H 1-2 H Cl H CF₂Cl H H 1-3H Br H CF₂Cl H H 1-4 H F H CF₂Cl CH₃ H 1-5 H Cl H CF₂Cl CH₃ H 1-6 H Br HCF₂Cl CH₃ H 1-7 F F H CF₂Cl H H 1-8 F Cl H CF₂Cl H H 1-9 F Br H CF₂Cl HH 1-10 F F H CF₂Cl CH₃ H 1-11 F Cl H CF₂Cl CH₃ H 1-12 F Br H CF₂Cl CH₃ H1-13 H F H CF₂Cl CH₃ NO₂ 1-14 H Cl H CF₂Cl CH₃ NO₂ 1-15 H Br H CF₂Cl CH₃NO₂ 1-16 F F H CF₂Cl CH₃ NO₂ 1-17 F Cl H CF₂Cl CH₃ NO₂ 1-18 F Br H CF₂ClCH₃ NO₂ 1-19 H F H CF₂Cl CH₃ NH₂ 1-20 H Cl H CF₂Cl CH₃ NH₂ 1-21 H Br HCF₂Cl CH₃ NH₂ 1-22 F F H CF₂Cl CH₃ NH₂ 1-23 F Cl H CF₂Cl CH₃ NH₂ 1-24 FBr H CF₂Cl CH₃ NH₂ 1-25 H F H CF₂Cl CH₃ OH 1-26 H Cl H CF₂Cl CH₃ OH 1-27H Br H CF₂Cl CH₃ OH 1-28 F F H CF₂Cl CH₃ OH 1-29 F Cl H CF₂Cl CH₃ OH1-30 F Br H CF₂Cl CH₃ OH 1-31 H Cl H CF₂Cl CH₃ NHCH₃ 1-32 H Cl H CF₂ClCH₃ NHC₂H₅ 1-33 H Cl H CF₂Cl CH₃ NHCH₂CH═CH₂ 1-34 H Cl H CF₂Cl CH₃NHCH₂C≡CH 1-35 H Cl H CF₂Cl CH₃ NHCH(CH₃)C≡CH 1-36 H Cl H CF₂Cl CH₃NHSO₂CH₃ 1-37 H Cl H CF₂Cl CH₃ NHSO₂C₂H₅ 1-38 H Cl H CF₂Cl CH₃NHSO₂CH₂Cl 1-39 H Cl H CF₂Cl CH₃ NHSO₂CF₃ 1-40 H Cl H CF₂Cl CH₃N(CH₃)SO₂CH₃ 1-41 H Cl H CF₂Cl CH₃ N(CH₂C≡CH)SO₂CH₃ 1-42 H Cl H CF₂ClCH₃ NHCOOCH₃ 1-43 H Cl H CF₂Cl CH₃ NHCOOC₂H 1-44 H Cl H CF₂Cl CH₃NHCOO^(n)C⁻ ₃H₇ 1-45 H Cl H CF₂Cl CH₃ NHCOO^(i)C₃H₇ 1-46 H Cl H CF₂ClCH₃ NHCOO^(n)C₄H₉ 1-47 H Cl H CF₂Cl CH₃ NHCOO^(n)C₅H₁₁ 1-48 H Cl H CF₂ClCH₃ NHCH₂COOCH₃ 1-49 H Cl H CF₂Cl CH₃ NHCH₂COOC₂H₅ 1-50 H Cl H CF₂Cl CH₃NHCH₂COO^(n)C₃H₇ 1-51 H Cl H CF₂Cl CH₃ NHCH₂COO^(n)C₄H₉ 1-52 H Cl HCF₂Cl CH₃ NHCH₂COO^(n)C₅H₁₁ 1-53 H Cl H CF₂Cl CH₃ NHCH₂COO^(i)C₃H₇ 1 54H Cl H CF₂Cl CH₃ NHCH₂COO^(c)C₅H₉ 1-55 H Cl H CF₂Cl CH₃NHCH₂COO_(c)C₆H₁₁ 1-56 H Cl H CF₂Cl CH₃ NHCH(CH₃)COOCH₃ 1-57 H Cl HCF₂Cl CH₃ NHCH(CH_(3 )COOC) ₂H₅ 1-58 H Cl H CF₂Cl CH₃ NHCH(CH_(3 )COO)^(n)C₃H₇ 1-59 H Cl H CF₂Cl CH₃ NHCH(CH_(3 )COO) ^(n)C₄H₉ 1-60 H Cl HCF₂Cl CH₃ NHCH(CH₃)COO^(n)C₅H₁₁ 1-61 H Cl H CF₂Cl CH₃NHCH(CH₃)COO^(i)C₃H₇ 1-62 H Cl H CF₂Cl CH₃ NHCH(CH₃)COO^(c)C₅H₉ 1-63 HCl H CF₂Cl CH₃ NHCH(CH₃)COO^(c)C₅H₁₁ 1-64 F Cl H CF₂Cl CH₃ NHCH₃ 1-65 FCl H CF₂Cl CH₃ NHC₂H₅ 1-66 F Cl H CF₂Cl CH₃ NHCH₂CH═CH₂ 1-67 F Cl HCF₂Cl CH₃ NHCH₂C≡CH 1-68 F Cl H CF₂Cl CH₃ NHCH(CH₃)C≡CH 1-69 F Cl HCF₂Cl CH₃ NHSO₂CH₃ 1-70 F Cl H CF₂Cl CH₃ NHSO₂C₂H₅ 1-71 F Cl H CF₂Cl CH₃NHSO₂CH₂Cl 1-72 F Cl H CF₂Cl CH₃ NHSO₂CF₃ 1-73 F Cl H CF₂Cl CH₃N(CH_(3 )SO) ₂CH₃. 1-74 F Cl H CF₂Cl CH₃ N(CH₂C≡CH)SO₂CH₃ 1-75 F Cl HCF₂Cl CH₃ NHCOOCH₃ 1-76 F Cl H CF₂Cl CH₃ NHCOOC₂H₅ 1-77 F Cl H CF₂Cl CH₃NHCO^(n)C₃H₇ 1-78 F Cl H CF₂Cl CH₃ NHCOO_(i)C₃H₇ 1-79 F Cl H CF₂Cl CH₃NHCOO_(n)C₄H₉ 1-80 F Cl H CF₂Cl CH₃ NHCOO_(n)C₅H₁₁ 1-81 F Cl H CF₂Cl CH₃NHCh₂COOCH₃ 1-82 F Cl H CF₂Cl CH₃ NHCH₂COOC₂H₅ 1-83 F Cl H CF₂Cl CH₃NHCH₂COO^(n)C₃H₇ 1-84 F Cl H CF₂Cl CH₃ NHCH₂COO^(n)C₄H₉ 1-85 F Cl HCF₂Cl CH₃ NHCH₂COO^(n)C₅H₁₁ 1-86 F Cl H CF₂Cl CH₃ NHCH₂COO^(i)C₃H₇ 1-87F Cl H CF₂Cl CH₃ NHCH₂COO^(c)C₅H₉ 1-88 F Cl H CF₂Cl CH₃NH₂CH₂COO^(c)C₆H₁₁ 1-89 F Cl H CF₂Cl CH₃ NHCH(CH₃)COOCH₃ 1-90 F Cl HCF₂Cl CH₃ NHCH(CH₃)COOC₂H₅ 1-91 F Cl H CF₂Cl CH₃ NHCH(CH₃)COO^(n)C₃H₇1-92 F Cl H CF₂Cl CH₃ NHCH(CH₃)COO^(n)C₄H₉ 1-93 F Cl H CF₂Cl CH₃NHCH(CH₃)COO^(n)C₅H₁₁ 1-94 F Cl H CF₂Cl CH₃ NHCH(CH₃)COO^(i)C₃H₇ 1-95 FCl H CF₂Cl CH₃ NHCH(CH₃)COO^(c)C₅H₉ 1-96 F Cl H CF₂Cl CH₃NHCH(CH₃)COO^(c)C₆H₁₁ 1-97 H Cl H CF₂Cl CH₃ OCH₃ 1-98 H Cl H CF₂Cl CH₃OC₂H₅ 1-99 H Cl H CF₂Cl CH₃ O^(i)C₃H₇ 1-100 H Cl H CF₂Cl CH₃ O^(n)C₃H₇1-101 H Cl H CF₂Cl CH₃ OCH₂CH₂Cl 1-102 H Cl H CF₂Cl CH₃ OCF₂CF₂H 1-103 HCl H CF₂Cl CH₃ O^(c)C₅H₆ 1-104 H Cl H CF₂Cl CH₃ O^(c)C₆H₁₁ 1-105 H Cl HCF₂Cl CH₃ OCH₂CH═CH₂ 1-106 H Cl H CF₂Cl CH₃ OCH₂CCl═CH₂ 1-107 H Cl HCF₂Cl CH₃ OCH₂CCl═CHCl 1-108 H Cl H CF₂Cl CH₃ OCH(CH₃)CH═CH₂ 1-109 H ClH CF₂Cl CH₃ OCH₂C≡CH 1-110 H Cl H CF₂Cl CH₃ OCH(CH₃)C≡CH 1-111 H Cl HCF₂Cl CH₃ OCH₂C≡CBr 1-112 H Cl H CF₂Cl CH₃ OCH₂C≡CCl 1-113 H Cl H CF₂ClCH₃ OCH₂C≡CCH₂Cl 1-114 H Cl H CF₂Cl CH₃ OCH₂CN 1-115 H Cl H CF₂Cl CH₃OCH₂OCH₃ 1-116 H Cl H CF₂Cl CH₃ OCH₂OC_(2 H) ₅ 1-117 H Cl H CF₂Cl CH₃OCH₂SCH₃ 1-118 H Cl H CF₂Cl CH₃ OCH₂COOCH₃ 1-119 H Cl H CF₂Cl CH₃OCH₂COOC₂H₃ 1-120 H Cl H CF₂Cl CH₃ OCH₂COO^(n)C₃H₇ 1-121 H Cl H CF₂ClCH₃ OCH₂COO^(n)C₄H₉ 1-122 H Cl H CF₂Cl CH₃ OCH₂COO^(n)C₅H₁₁ 1-123 H Cl HCF₂Cl CH₃ OCH₂COO^(i)C₃H₇ 1-124 H Cl H CF₂Cl CH₃ OCH₂COO^(c)C₅H₉ 1-125 HCl H CF₂Cl CH₃ OC₂COO^(c)C₆H₁₁ 1-126 H Cl H CF₂Cl CH₃ OCH(CH₈)COOCH₈1-127 H Cl H CF₂Cl CH₃ OCH(CH₃)COOC₂H₅ 1-128 H Cl H CF₂Cl CH₃OCH(CH₃)COO^(n)C₃H₇ 1-129 H Cl H CF₂Cl CH₃ OCH(CH₃)COO^(n)C₄H₉ 1-130 HCl H CF₂Cl CH₃ OCH(CH₃)COO^(n)C₅H₁₁ 1-131 H Cl H CF₂Cl CH₃OCH(CH₃)COO^(i)C₃H₇ 1-132 H Cl H CF₂Cl CH₃ OCH(CH₃)COO^(c)C₅H₉ 1-133 HCl H CF₂Cl CH₃ OCH(CH₃)COO^(c)C₆H₁₁ 1-134 H Cl H CF₂Cl CH₃ OCH₂CON(CH₃)₂1-135 H Cl H CF₂Cl CH₃ OCH₂CON(C₂H₅)₂ 1-136 H Cl H CF₂Cl CH₃OCH₂CON(CH₃)C₂H₅ 1-137 H Cl H CF₂Cl CH₃ OCH(CH₃)CON(CH₃)₂ 1-138 H Cl HCF₂Cl CH₃ OCH(CH₃)CON(C₂H₅ 1-139 H Cl H CF₂Cl CH₃ OCH(CH₃)CON(CH₃)C₂H₅1-140 H Cl H CF₂Cl CH₃ OCH₂COON(CH₃)₂ 1-141 H Cl H CF₂Cl CH₃OCH₂COON(C₂H₅)₂ 1-142 H Cl H CF₂Cl CH₃ OCH(CH₃)COON(CH₃)₂ 1-143 H Cl HCF₂Cl CH₃ OCH(CH₃)COON(C₂H₅)₂ 1-144 F Cl H CF₂Cl CH₃ OCH₃ 1-145 F Cl HCF₂Cl CH₃ OC₂H₅ 1-146 F Cl H CF₂Cl CH₃ O^(i)C₃H₇ 1-147 F Cl H CF₂Cl CH₃O^(n)C₃H₇ 1-148 F Cl H CF₂Cl CH₃ OCH₂CH₂Cl 1-149 F Cl H CF₂Cl CH₃OCF₂CF₂H 1-150 F Cl H CF₂Cl CH₃ O^(c)C₆H₉ 1-151 F Cl H CF₂Cl CH₃O_(c)C₆H₁₁ 1-152 F Cl H CF₂Cl CH₃ OCH₂CH₂═CH₂ 1-153 F Cl H CF₂Cl CH₃OCH₂CCl═CH₂ 1-154 F Cl H CF₂Cl CH₃ OCH₂CCl═CHCl 1-155 F Cl H CF₂Cl CH₃OCH(CH₃)CH═CH₂ 1-156 F Cl H CF₂Cl CH₃ OCH₂C≡CH 1-157 F Cl H CF₂Cl CH₃OCH(CH₃)C≡CH 1-158 F Cl H CF₂Cl CH₃ OCH₂C≡CBr 1-159 F Cl H CF₂Cl CH₃OCH₂C≡CCl 1-160 F Cl H CF₂Cl CH₃ OCH₂C≡CCH₂Cl 1-161 F Cl H CF₂Cl CH₃OCH₂CN 1-162 F Cl H CF₂Cl CH₃ OCH₂OCH 1-163 F Cl H CF₂Cl CH₃ OCH₂OC₂H₅1-164 F Cl H CF₂Cl CH₃ OCH₂SCH₃ 1-165 F CL H CF₂Cl CH₃ OCH₂COOCH₃ 1-166F Cl H CF₂Cl CH₃ OCH₂COOC₂H₅ 1-167 F Cl H CF₂Cl CH₃ OCH₂COO^(n)C₃H₇1-168 F Cl H CF₂Cl CH₃ OCH₂COO^(n)C₄H₉ 1-169 F Cl H CF₂Cl CH₃OCH₂COO^(n)C₅H₁₁ 1-170 F Cl H CF₂Cl CH₃ OCH₂COO^(i)C₃H₇ 1-171 F Cl HCF₂Cl CH₃ OCH₂COO^(c)C₅H₉ 1 172 F Cl H CF₂Cl CH₃ OCH₂COO^(c)C₈H₁₁ 1-173F Cl H CF₂Cl CH₃ OCH(CH₃)COOCH₃ 1-174 F Cl H CF₂Cl CH₃ OCH(CH₃)COOC₂H₅1-175 F Cl H CF₂Cl CH₃ OCH(CH₃)COO_(n)C₃H₇ 1-176 F Cl H CF₂Cl CH₃OCH(CH₃)COO_(n)C₄H₉ 1-177 F Cl H CF₂Cl CH₃ OCH(CH₃)COO_(n)C₅H₁₁ 1-178 FCl H CF₂Cl CH₃ OCH(CH₃)COO^(i)C₃H₇ 1-179 F Cl H CF₂Cl CH₃OCH(CH₃)COO^(c)C₅H₉ 1-180 F Cl H CF₂Cl CH₃ OCH(CH₃)COO^(c)C₆H₁₁ 1-181 FCl H CF₂Cl CH₃ OCH₂CON(CH₃)₂ 1-182 F Cl H CF₂Cl CH₃ OCH₂CON(C₂H₅)₂ 1-183F Cl H CF₂Cl CH₃ OCH₂CON(CH₃)C₂H₅ 1-184 F Cl H CF₂Cl CH₃OCH(CH₃)CON(CH₃)₂ 1-185 F Cl H CF₂Cl CH₃ OCH(CH₃)CON(C₂H₅) 1-186 F Cl HCF₂Cl CH₃ OCH(CH₃)CON(CH₃)C₂H₅ 1-187 F Cl H CF₂Cl CH₃ OCH₂COON(CH₃)₂1-188 F Cl H CF₂Cl CH₃ OCH₂COON(C₂H₅) 1-189 F Cl H CF₂Cl CH₃OCH(CH₃)COON(CH₃)₂ 1-190 F Cl H CF₂Cl CH₃ OCH(CH₃)COON(C₂H₅)₂ 1-191 H FH CF₂Cl CH₃ SH 1-192 H Cl H CF₂Cl CH₃ SH 1-193 H Br H CF₂Cl CH₃ SH 1-194F F H CF₂Cl CH₃ SH 1-195 F Cl H CF₂Cl CH₃ SH 1-196 F Br H CF₂Cl CH₃ SH1-197 H Cl H CF₂Cl CH₃ SCH₃ 1-198 H Cl H CF₂Cl CH₃ SC₂H₅ 1-199 H Cl HCF₂Cl CH₃ S^(i)C₃H₇ 1-200 H Cl H CF₂Cl CH₃ SCH₂CH₂Cl 1-201 H Cl H CF₂ClCH₃ S^(c)C₅H₉ 1-202 H Cl H CF₂Cl CH₃ S^(c)C₆H₁₁ 1-203 H Cl H CF₂Cl CH₃SCH₂CH═CH₂ 1-204 H Cl H CF₂Cl CH₃ SCH₂CCl═CH₂ 1-205 H Cl H CF₂Cl CH₃SCH₂CCl═CHCl 1-206 H Cl H CF₂Cl CH₃ SCH(CH₃)CH═CH₂ 1-207 H Cl H CF₂ClCH₃ SCH₂C≡CH 1-208 H Cl H CF₂Cl CH₃ SCH(CH₃)C≡CH 1-209 H Cl H CF₂Cl CH₃SCH₂COOCH₃ 1-210 H Cl H CF₂Cl CH₃ SCH₂COOC₂H₅ 1-211 H Cl H CF₂Cl CH₃SCH₂COO^(n)C₃H₇ 1 212 H Cl H CF₂Cl CH₃ SCH₂COO^(n)C₄H₉ 1-213 H Cl HCF₂Cl CH₃ SCH₂COO^(n)C₅H₁₁ 1-214 H Cl H CF₂Cl CH₃ SCH₂COO^(i)C₃H₇ 1-215H Cl H CF₂Cl CH₃ SCH₂COO^(c)C₅H₉ 1-216 H Cl H CF₂Cl CH₃ SCH₂COO^(c)C₆H₁₁1-217 H Cl H CF₂Cl CH₃ SCH(CH₃)COOCH₃ 1-218 H Cl H CF₂Cl CH₃SCH(CH₃)COOC₂H₅ 1-219 H Cl H CF₂Cl CH₃ SCH(CH₃)COO^(n)C₃H₇ 1-220 H Cl HCF₂Cl CH₃ SCH(CH₃)COO^(n)C₄H₉ 1-221 H Cl H CF₂Cl CH₃SCH(CH₃)COO^(n)C₅H₁₁ 1-222 H Cl H CF₂Cl CH₃ SCH(CH₃)COO^(i)C₃H₇ 1-223 HCl H CF₂Cl CH₃ SCH(CH₃)COO^(c)C₅H₉ 1-224 H Cl H CF₂Cl CH₃SCH(CH₃)COO^(c)C₆H₁₁ 1-225 H Cl H CF₂Cl CH₃ SCH₂CON(CH₃)₂ 1-226 H Cl HCF₂Cl CH₃ SCH₂CON(C₂H₅)₂ 1-227 H Cl H CF₂Cl CH₃ SCH₂CON(tetramethylene)1-228 H Cl H CF₂Cl CH₃ SCH₂CON(pentamethylene) 1-229 H Cl H CF₂Cl CH₃SCH₂CON (ethyleneoxyethylene) 1-230 H Cl H CF₂Cl CH₃ SCH(CH₃)CON(CH₃)₂1-231 H Cl H CF₂Cl CH₃ SCH(CH₃)CON(C₂H₅)₂ 1-232 H Cl H CF₂Cl CH₃SCH(CH₃)CON (tetramethylene) 1-233 H Cl H CF₂Cl CH₃ SCH(CH₃)CON(pentamethylene) 1-234 F Cl H CF₂Cl CH₃ SCH₃ 1-235 F Cl H CF₂Cl CH₃SC₂H₅ 1-236 F Cl H CF₂Cl CH₃ S^(i)C₃H₇ 1-237 F Cl H CF₂Cl CH₃ SCH₂CH₂Cl1-238 F Cl H CF₂Cl CH₃ S^(c)C₅H₉ 1-239 F Cl H CF₂Cl CH₃ S^(c)C₆H₁₁ 1-240F CL H CF₂Cl CH₃ SCH₂CH═CH₂ 1-241 F Cl H CF₂Cl CH₃ SCH₂CCl═CH₂ 1-242 FCL H CF₂Cl CH₃ SCH₂CCl═CHCl 1-243 F CL H CF₂Cl CH₃ SCH(CH₃)CH═CH₂ 1-244F Cl H CF₂Cl CH₃ SCH₂C≡CH 1-245 F Cl H CF₂Cl CH₃ SCH(CH₃)C≡CH 1-246 F ClH CF₂Cl CH₃ SCH₂COOCH₃ 1-247 F Cl H CF₂Cl CH₃ SCH₂COOC₂H₅ 1-248 F Cl HCF₂Cl CH₃ SCH₂COO^(n)C₃H₇ 1-249 F Cl H CF₂Cl CH₃ SCH₂COO^(n)C₄H₉ 1-250 FCl H CF₂Cl CH₃ SCH₂COO^(n)C₅H₁₁ 1-251 F Cl H CF₂Cl CH₃ SCH₂COO^(i)C₃H₇1-252 F Cl H CF₂Cl CH₃ SCH₂COO^(c)C₅H₉ 1-253 F Cl H CF₂Cl CH₃SCH₂COO^(c)C₆H₁₁ 1-254 F Cl H CF₂Cl CH₃ SCH(CH₃)COOCH₃ 1-255 F Cl HCF₂Cl CH₃ SCH(CH₃)COOC₂H₅ 1-256 F Cl H CF₂Cl CH₃ SCH(CH₃)COO^(n)C₃H₇1-257 F Cl H CF₂Cl CH₃ SCH(CH₃)COO^(n)C₄H₉ 1-258 F Cl H CF₂Cl CH₃SCH(CH₃)COO^(n)C₅H₁₁ 1-259 F Cl H CF₂Cl CH₃ SCH(CH₃)COO^(i)C₃H₇ 1-260 FCl H CF₂Cl CH₃ SCH(CH₃)COO^(c)C₅H₉ 1-261 F C H CF₂Cl CH₃SCH(CH₃)COO^(c)C₆H₁₁ 1-262 F Cl H CF₂Cl CH₃ SCH₂CON(CH₃ ₎ ₂ 1-263 F Cl HCF₂Cl CH₃ SCH₂CON(CH₃)₂ 1-264 F Cl H CF₂Cl CH₃ SCH₂CON(tetramethylene)1-265 F Cl H CF₂Cl CH₃ SCH₂CON(pentamethylene) 1-266 F Cl H CF₂Cl CH₃SCH₂CON (etHyleneoxyetHylene) 1-267 F Cl H CF₂Cl CH₃ SCH(CH₃)CON(CH₃)₂1-268 F Cl H CF₂Cl CH₃ SCH(CH₃)CON(C₂H₅)₂ 1-269 F Cl H CF₂Cl CH₃SCH(CH₃)CON (tetrametHylene) 1-270 F Cl H CF₂Cl CH₃ SCH(CH₃)CON(pentainetHylene) 1-271 H F H CF₂Cl CH₃ SO₂Cl 1-272 H Cl H CF₂Cl CH₃SO₂Cl 1-273 H Br H CF₂Cl CH₃ SO₂Cl 1-274 F F H CF₂Cl CH₃ SO₂Cl 1-275 FCl H CF₂Cl CH₃ SO₂Cl 1-276 F Br H CF₂Cl CH₃ SO₂Cl 1-277 H Cl H CF₂Cl CH₃SO₂OCH₃ 1-278 H Cl H CF₂Cl CH₃ SO₂OC₂H₅ 1-279 H Cl H CF₂Cl CH₃SO₂O^(i)C₃H₇ 1-280 H Cl H CF₂Cl CH₃ SO₂OCH₂CH═CH₂ 1-281 F Cl H CF₂Cl CH₃SO₂OCH₃ 1-282 F Cl H CF₂Cl CH₃ SO₂OC₂H₅ 1-283 F Cl H CF₂Cl CH₃SO₂O^(i)C₃H₇ 1-284 F Cl H CF₂Cl CH₃ SO₂OCH₂CH═CH₂ 1-285 H Cl H CF₂Cl CH₃SO₂N(CH₃)₂ 1-286 H Cl H CF₂Cl CH₃ SO₂N(C₂H₅)₂ 1-287 F Cl H CF₂Cl CH₃SO₂N(CH₃)₂ 1-288 F Cl H CF₂Cl CH₃ SO₂N(C₂H₅)₂ 1-289 H Cl H CF₂Cl CH₃COOH 1-290 H Cl H CF₂Cl CH₃ COOCH₃ 1-291 H Cl H CF₂Cl CH₃ COOC₂H₅ 1-292H Cl H CF₂Cl CH₃ COO^(n)C₃H₇ 1-293 H Cl H CF₂Cl CH₃ COO^(n)C₄H₉ 1-294 HCl H CF₂Cl CH₃ COO^(n)C₅H₁₁ 1-295 H Cl H CF₂Cl CH₃ COO^(i)C₃H₇ 1-296 HCl H CF₂Cl CH₃ COOCH₂CH₂Cl 1-297 H Cl H CF₂Cl CH₃ COOCH₂CH₂Br 1-298 H ClH CF₂Cl CH₃ CON(CH₃)₂ 1-299 H Cl H CF₂Cl CH₃ CONHCH₃ 1-300 H Cl H CF₂ClCH₃ CON(C₂H₅)₂ 1-301 H Cl H CF₂Cl CH₃ CONHC₂H₅ 1-302 H Cl H CF₂Cl CH₃COCH₃ 1-303 H Cl H CF₂Cl CH₃ COC₂H₅ 1-304 H Cl H CF₂Cl CH₃ COCH₂Cl 1-305H Cl H CF₂Cl CH₃ CHO 1-306 H Cl H CF₂Cl CH₃ CH═CHCOOCH₃ 1-307 H Cl HCF₂Cl CH₃ CH═CHCOOC₂H₅ 1-308 H Cl H CF₂Cl CH₃ CH₂CH₂COOCH₃ 1-309 H Cl HCF₂Cl CH₃ CH₂CH₂COOC₂H₅ 1-310 F Cl H CF₂Cl CH₃ COOH 1-311 F Cl H CF₂ClCH₃ COOCH₃ 1-312 F Cl H CF₂Cl CH₃ COOC₂H₅ 1-313 F Cl H CF₂Cl CH₃COO^(n)C₃H₇ 1-314 F Cl H CF₂Cl CH₃ COO^(n)C₄H₉ 1-315 F Cl H CF₂Cl CH₃COO^(n)C₅H₁₁ 1-316 F Cl H CF₂Cl CH₃ COO^(i)C₃H₇ 1-317 F Cl H CF₂Cl CH₃COOCH₂CH₂Cl 1-318 F Cl H CF₂Cl CH₃ COOCH₂CH₂Br 1-319 F Cl H CF₂Cl CH₃CON(CH₃)₂ 1-320 F Cl H CF₂Cl CH₃ CONHCH₃ 1-321 F Cl H CF₂Cl CH₃CON(C₂H₅)₂ 1-322 F Cl H CF₂Cl CH₃ CONHC₂H₅ 1-323 F Cl H CF₂Cl CH₃ COCH₃1-324 F Cl H CF₂Cl CH₃ COC₂H₅ 1-325 F Cl H CF₂Cl CH₃ COCH₂Cl 1-326 F ClH CF₂Cl CH₃ CHO 1-327 F Cl H CF₂Cl CH₃ CH═CHCOOCH₃ 1-328 F Cl H CF₂ClCH₃ CH═CHCOOC₂H₅ 1-329 F Cl H CF₂Cl CH₃ CH₂CH₂COOCH₃ 1-330 F Cl H CF₂ClCH₃ CH₂CH₂COOC₂H₅ 1-331 H F H CF₃ H H 1-332 H Cl H CF₃ H H 1-333 H Br HCF₃ H H 1-334 H F H CF₃ CH₃ H 1-335 H Cl H CF₃ CH₃ H 1-336 H Br H CF₃CH₃ H 1-337 F F H CF₃ H H 1-338 F Cl H CF₃ H H 1-339 F Br H CF₃ H H1-340 F F H CF₃ CH₃ H 1-341 F Cl H CF₃ CH₃ H 1-342 F Br H CF₃ CH₃ H1-343 H F H CF₃ CH₃ NO₂ 1-344 H Cl H CF₃ CH₃ NO₂ 1-345 H Br H CF₃ CH₃NO₂ 1-346 F F H CF₃ CH₃ NO₂ 1-347 F Cl H CF₃ CH₃ NO₂ 1-348 F Br H CF₃CH₃ NO₂ 1-349 H F H CF₃ CH₃ NH₂ 1-350 H Cl H CF₃ CH₃ NH₂ 1-351 H Br HCF₃ CH₃ NH₂ 1-352 F F H CF₃ CH₃ NH₂ 1-353 F Cl H CF₃ CH₃ NH₂ 1-354 H ClH CF₃ CH₃ NHCH(CH₃)COOCH₃ 1-355 H Cl H CF₃ CH₃ NHCH(CH₃)COOC₂H₅ 1-356 HCL H CF₃ CH₃ NHCH(CH₃)COO^(n)C₃H₇ 1-357 H Cl H CF₃ CH₃NHCH(CH₃)COO^(n)C₄H₉ 1-358 H Cl H CF₃ CH₃ NHCH(CH₃)COO^(n)C₅H₁₁ 1-359 HCl H CF₃ CH₃ NHCH(CH₃)COO^(i)C₃H₇ 1-360 H Cl H CF₃ CH₃NHCH(CH₃)COO^(c)C₅H₉ 1-361 H Cl H CF₃ CH₃ NHCH(CH₃)COO^(c)C₆H₁₁ 1-362 FCl H CF₃ CH₃ NHCH₃ 1-363 F Cl H CF₃ CH₃ NHC₂H₅ 1-364 F Cl H CF₃ CH₃NHCH₂CH═CH₂ 1-365 F Cl H CF₃ CH₃ NHCH₂C≡CH 1-366 F Cl H CF₃ CH₃NHCH(CH₃)C≡CH 1-367 F Cl H CF₃ CH₃ NHSO₂CH₃ 1-368 F Cl H CF₃ CH₃NHSO₂C₂H₅ 1-369 F Cl H CF₃ CH₃ NHSO₂CH₂Cl 1-370 F Cl H CF₃ CH₃ NHSO₂CF₃1-371 F Cl H CF₃ CH₃ N(CH₃)SO₂CH₃ 1-372 F Cl H CF₃ CH₃ N(CH₂C≡CH)SO₂CH₃1-373 F Cl H CF₃ CH₃ NHCOOCH₃ 1-374 F Cl H CF₃ CH₃ NHCOOC₂H₃ 1-375 F ClH CF₃ CH₃ NHCOO^(n)C₃H₇ 1-376 F Cl H CF₃ CH₃ NHCOO^(i)C₃H₇ 1-377 F Cl HCF₃ CH₃ NHCOO^(n)C₄H₉ 1-378 F Cl H CF₃ CH₃ NHCOO^(n)C₅H₁₁ 1-379 F Cl HCF₃ CH₃ NHCH₂COOCH₃ 1-380 F Cl H CF₃ CH₃ NHCH₂COOC₂H₅ 1-381 F Cl H CF₃CH₃ NHCH₂COO^(n)C₃H₇ 1-382 F Cl H CF₃ CH₃ NHCH₂COO^(n)C₄H₉ 1-383 F Cl HCF₃ CH₃ NHCH₂COO^(n)C₅H₁₁ 1-384 F Cl H CF₃ CH₃ NHCH₂COO^(i)C₃H₇ 1-385 FCl H CF₃ CH₃ NHCH₂COO^(c)C₅H₉ 1-386 F Br H CF₃ CH₃ NH₂ 1-387 H F H CF₃CH₃ OH 1-388 H Cl H CF₃ CH₃ OH 1-389 H Br H CF₃ CH₃ OH 1-390 F F H CF₃CH₃ OH 1-391 F Cl H CF₃ CH₃ OH 1-392 F Br H CF₃ CH₃ OH 1-393 H Cl H CF₃CH₃ NHCH₃ 1-394 H Cl H CF₃ CH₃ NHC₂H₃ 1-395 H Cl H CF₃ CH₃ NHCH₂CH═CH₂1-396 H Cl H CF₃ CH₃ NHCH₂C≡CH 1-397 H Cl H CF₃ CH₃ NHCH(CH₃)C≡CH 1-398H Cl H CF₃ CH₃ NHSO₂CH₃ 1-399 H Cl H CF₃ CH₃ NHSO₂C₂H₅ 1-400 H Cl H CF₃CH₃ NHSO₂CO₂Cl 1-401 H Cl H CF₃ CH₃ NOSO₂CF₃ 1-402 H Cl H CF₃ CH₃N(CH₃)SO₂CH₃ 1-403 H Cl H CF₃ CH₃ N(CH₂C≡CH)SO₂CH₃ 1-404 H Cl H CF₃ CH₃NHCOOCH₃ 1-405 H Cl H CF₃ CH₃ NHCOOC₂H₅ 1-406 H Cl H CF₃ CH₃NHCOO^(n)C₃H₇ 1-407 H Cl H CF₃ CH₃ NOCOO^(i)C₃H₇ 1-408 H Cl H CF₃ CH₃NHCOO^(n)C₄H₉ 1-409 H Cl H CF₃ CH₃ NHCOO^(n)C₅H₁₁ 1-410 H Cl H CF₃ CH₃NHCH₂COOCH₃ 1-411 H Cl H CF₃ CH₃ NHCH₂COOC₂H₃ 1-412 H Cl H CF₃ CH₃NHCH₂COO^(n)C₃H₇ 1-413 H Cl H CF₃ CH₃ NHCH₂COO^(n)C₄H₉ 1-414 H Cl H CF₃CH₃ NHCH₂COO^(n)C₅H₁₁ 1-415 H Cl H CF₃ CH₃ NHCH₂COO^(i)C₃H₇ 1-416 H Cl HCF₃ CH₃ NHCH₂COO^(c)C₅H₉ 1-417 H Cl H CF₃ CH₃ NHCH₂COO^(c)C₆H₁₁ 1-418 FCl H CF₃ CH₃ NH CH₂COO^(c)C₆H₁₁ 1-419 F Cl H CF₃ CH₃ NHCH(CH₃)COOCH₃1-420 F Cl H CF₃ CH₃ NHCH(CH₃)COOC₂H₃ 1-421 F Cl H CF₃ CH₃NHCH(CH₃)COO^(n)C₃H₃ 1-422 F Cl H CF₃ CH₃ NHCH(CH₃)COO^(n)C₄H₉ 1-423 FCl H CF₃ CH₃ NHCH(CH₃)COO^(n)C₅H₁₁ 1-424 F Cl H CF₃ CH₃NHCH(CH₃)COO^(i)C₃H₇ 1-425 F Cl H CF₃ CH₃ NHCH(CH₃)COO^(c)C₅H₉ 1-426 FCl H CF₃ CH₃ NHCH(CH₃)COO^(c)C₆H₁₁ 1-427 H Cl H CF₃ CH₃ OCH₃ 1-428 H ClH CF₃ CH₃ OC₂H₅ 1-429 H Cl H CF₃ CH₃ O^(i)C₃H₇ 1-430 H Cl H CF₃ CH₃O^(n)C₃H₇ 1-431 H Cl H CF₃ CH₃ OCH₂CH₂Cl 1-432 H Cl H CF₃ CH₃ OCF₂CF₂H1-433 H Cl H CF₃ CH₃ O^(c)C₅H₉ 1-434 H Cl H CF₃ CH₃ O^(c)C₆H₁₁ 1-435 HCl H CF₃ CH₃ OCH₂CH═CH₂ 1-436 H Cl H CF₃ CH₃ OCH₂CCl═CH₂ 1-437 H Cl HCF₃ CH₃ OCH₂CCl═CHCl 1-438 H Cl H CF₃ CH₃ OCH(CH₃)CH═CH₂ 1-439 H Cl HCF₃ CH₃ OCH₂C≡CH 1-440 H Cl H CF₃ CH₃ OCH(CH₃)C≡CH 1-441 H Cl H CF₃ CH₃OCh₂C≡CBr 1-442 H Cl H CF₃ CH₃ OCH₂C≡CCl 1-443 H Cl H CF₃ CH₃OCH₂C≡CCH₂Cl 1-444 H Cl H CF₃ CH₃ OCH₂CN 1-445 H Cl H CF₃ CH₃ OCH₂OCH₃1-446 H Cl H CF₃ CH₃ OCH₂OC₂H₅ 1-447 H Cl H CF₃ CH₃ OCH₂SCH₃ 1-448 H ClH CF₃ CH₃ OCH₂COOCH₃ 1-449 H Cl H CF₃ CH₃ OCH₂COOC₂H₃ 1-450 H Cl H CF₃CH₃ OCH₂COO^(n)C₃H₇ 1-451 H Cl H CF₃ CH₃ OCH₂COO^(n)C₄H₉ 1-452 H Cl HCF₃ CH₃ OCH₂COO^(n)C₅H₁₁ 1-453 H Cl H CF₃ CH₃ OCH₂COO^(i)C₃H₇ 1-454 H ClH CF₃ CH₃ OCH₂COO^(c)C₅H₉ 1-455 H Cl H CF₃ CH₃ OCH₂COO^(c)C₆H₁₁ 1-456 HCl H CF₃ CH₃ OCH(CH₃)COOCH₃ 1-457 H Cl H CF₃ CH₃ OCH(CH₃)COOC₂H₃ 1-458 HCl H CF₃ CH₃ OCH(CH₃)COO^(n)C₃H₇ 1-459 H Cl H CF₃ CH₃OCH(CH₃)COO^(n)C₄H₉ 1-460 H Cl H CF₃ CH₃ OCH(CH₃)COO^(n)C₅H₁₁ 1-461 H ClH CF₃ CH₃ OCH(CH₃)COO^(i)C₃H₃ 1-462 H Cl H CF₃ CH₃ OCH(CH₃)COO^(c)C₅H₉1-463 H Cl H CF₃ CH₃ OCH(CH₃)COO^(c)C₆H₁₁ 1-464 H Cl H CF₃ CH₃OCH₂CON(CH₃)₂ 1-465 H Cl H CF₃ CH₃ OCH₂CON(C₂H₅)₂ 1-466 H Cl H CF₃ CH₃OCH₂CON(CH₃)C₂H₃ 1-467 H Cl H CF₃ CH₃ OCH(CH₃)CON(CH₃)₂ 1-468 H Cl H CF₃CH₃ OCH(CH₃)CON(C₂H₃ 1-469 H Cl H CF₃ CH₃ OCH(CH₃)CON(CH₃)C₂H₅ 1-470 HCl H CF₃ CH₃ OCH₂COON(CH₃₎ ₂ 1-471 H Cl H CF₃ CH₃ OCH₂COON(C₂H₃ 1-472 HCl H CF₃ CH₃ OCH(CH₃)COON(CH₃)₂ 1-473 H Cl H CF₃ CH₃ OCH(CH₃)COON(C₂H₅)₂1-474 F Cl H CF₃ CH₃ OCH₃ 1-475 F Cl H CF₃ CH₃ OC₂H₅ 1-476 F Cl H CF₃CH₃ O^(i)C₃H₇ 1-477 F Cl H CF₃ CH₃ O^(n)C₃H₇ 1-478 F Cl H CF₃ CH₃OCH₂CH₂Cl 1-479 F Cl H CF₃ CH₃ OCF₂CF₂H 1-480 F Cl H CF₃ CH₃ O_(c)C₅H₉1-481 F Cl H CF₃ CH₃ O^(c)C₆H₁₁ 1-482 F Cl H CF₃ CH₃ OCH₂CH═CH₂ 1-483 FCl H CF₃ CH₃ OCH₂CCl═CH₂ 1-484 F Cl H CF₃ CH₃ OCH₂CCl═CHCl 1-485 F Cl HCF₃ CH₃ OCH(CH₃)CH═CH₂ 1-486 F Cl H CF₃ CH₃ OCH₂C≡CH 1-487 F Cl H CF₃CH₃ OCH(Ch₃)C≡CH 1-488 F Cl H CF₃ CH₃ OCH₂C≡CBr 1-489 F Cl H CF₃ CH₃OCH₂C≡CCl 1-490 F Cl H CF₃ CH₃ OCH₂C≡CCH₂Cl 1-491 F Cl H CF₃ CH₃ OCH₂CN1-492 F Cl H CF₃ CH₃ OCH₂OCH₃ 1-493 F Cl H CF_(3 CH) ₃ OCH₂OC₂H₃ 1-494 FCl H CF₃ CH₃ OCH₂SCH₃ 1-495 F Cl H CF₃ CH₃ OCH₂COOCH₃ 1-496 F Cl HCF_(3 CH) ₃ OCH₂COOC₂H₃ 1-497 F Cl H CF₃ CH₃ OCH₂COO^(n)C₃H₇ 1-498 F ClH CF₃ CH₃ OCH₂COO^(n)C₄H₉ 1-499 F Cl H CF₃ CH₃ OCH₂COO^(n)C₅H₁₁ 1-500 FCl H CF₃ CH₃ OCH₂COO^(i)C₃H₇ 1-501 F Cl H CF₃ CH₃ OCH₂COO^(c)C₅H₉ 1-502F Cl H CF₃ CH₃ OCH₂COO^(c)C₆H₁₁ 1-503 F Cl H CF₃ CH₃ OCH(CH₃)COOCH₃1-504 F Cl H CF₃ CH₃ OCH(CH₃)COOC₂H₅ 1-505 F Cl H CF₃ CH₃OCH(Ch₃)COO^(n)C₃H₇ 1-506 F Cl H CF₃ CH₃ OCH(Ch₃)COO^(n)C₄H₉ 1-507 F ClH CF₃ CH₃ OCH(CH₃)COO^(n)C₅H₇ 1-508 F Cl H CF_(3 CH) ₃OCH(CH₃)COO^(i)C₃H₇ 1-509 F Cl H CF_(3 CH) ₃ OCH(CH₃)COO^(c)C₅H₃ 1-510 FCl H CF₃ CH₃ OCH(CH₃)COO^(c)C₆H₁₁ 1-511 F Cl H CF₃ CH₃ OCH₂CON(CH₃)₃1-512 F Cl H CF₃ CH₃ OCH₂CON(C₂H₅)₂ 1-513 F Cl H CF₃ CH₃OCH₂CON(CH₃)C₂H₃ 1-514 F Cl H CF₃ CH₃ OCH(CH₃)CON(CH 3)₂ 1-515 F Cl HCF₃ CH₃ OCH(CH₃)CON(C₂H₅)₂ 1-516 F Cl H CF₃ CH₃ OCH(CH₃)CON(CH₃)C₂H₅1-517 F Cl H CF₃ CH₃ OCH₂COON(CH⁻ ₃)₂ 1-518 F Cl H CF₃ CH₃OCH₂COON(C₂H₅)₂ 1-519 F Cl H CF₃ CH₃ OCH(CH₃)COON(CH₃)₂ 1-520 F Cl H CF₃CH₃ OCH(CH₃)COON(C₂H₅)₂ 1-521 H F H CF₃ CH₃ SH 1-522 H Cl H CF₃ CH₃ SH1-523 H Br H CF₃ CH₃ SH 1-524 F F H CF₃ CH₃ SH 1-525 F Cl H CF₃ CH₃ SH1-526 F Br H CF₃ CH₃ SH 1-527 H Cl H CF₃ CH₃ SCH₃ 1-528 H Cl H CF₃ CH₃SC₂H₅ 1-529 H Cl H CF₃ CH₃ S^(i)C₃H₇ 1-530 H Cl H CF₃ CH₃ SCH₂CH₂Cl1-531 H Cl H CF₃ CH₃ S_(c)C₅H₉ 1-532 H Cl H CF₃ CH₃ S_(c)C₆H₁₁ 1-533 HCl H CF₃ CH₃ SCH₂CH═CH₂ 1-534 H Cl H CF₃ CH₃ SCH₂CCl═CH₂ 1-535 H Cl HCF₃ CH₃ SCH₂CCl=CHCl 1-536 H Cl H CF₃ CH₃ SCH(CH₃)CH═CH₂ 1-537 H Cl HCF₃ CH₃ SCH₂C≡CH 1-538 H Cl H CF₃ CH₃ SCH(CH₃)C≡CH 1-539 H Cl H CF₃ CH₃SCH₂COOCH₃ 1-540 H Cl H CF₃ CH₃ SCH₂COOC₂H₅ 1-541 H Cl H CF₃ CH₃SCH₂COO^(n)C₃H₇ 1-542 H Cl H CF₃ CH₃ SCH₂COO^(n)C₄H₉ 1-543 H Cl H CF₃CH₃ SCH₂COO^(n)C₅H₁₁ 1-544 H Cl H CF₃ CH₃ SCH₂COO^(i)C₃H₇ 1-545 H Cl HCF₃ CH₃ SCH₂COO^(c)C₅H₉ 1-546 H Cl H CF₃ CH₃ SCH₂COO^(c)C₆H₁₁ 1 547 H ClH CF₃ CH₃ SCH(CH₃)COOCH₃ 1-548 H Cl H CF₃ CH₃ SCH(CH₃)COOC₂H₃ 1-549 H ClH CF₃ CH₃ SCH(CH₃)COO^(n)C₃H₇ 1-550 H Cl H CF₃ CH₃ SCH(CH₃)COO^(n)C₄H₉1-551 H Cl H CF₃ CH₃ SCH(CH₃)COO^(n)C₅H₁₁ 1-552 H Cl H CF₃ CH₃SCH(CH₃)COO^(i)C₃H₇ 1-553 H Cl H CF₃ CH₃ SCH(CH₃)COO^(c)C₅H₉ 1-554 H ClH CF₃ CH₃ SCM(CH₃)COO^(c)C₆H₁₁ 1-555 H Cl H CF₃ CH₃ SCH₂CON(CH₃)₂ 1-556H Cl H CF₃ CH₃ SCH₂CON(C₂H₅)₂ 1 557 H Cl H CF₃ CH₃SCH₂CON(tetramethylene) 1-558 H Cl H CF₃ CH₃ SCH₂CON(pentamethylene)1-559 H Cl H CF₃ CH₃ SCH₂CON (ethyleneoxyethylene) 1-560 H Cl H CF₃ CH₃SCH(CH₃)CON(CH₃)₃ 1-561 H Cl H CF₃ CH₃ SCH(CH₃)CON(C₂H₅)₃ 1-562 H Cl HCF₃ CH₃ SCH(CH₃)CON (tetramethylene) 1-563 H Cl H CF₃ CH₃ SCH(CH₃)CON(pentamethylene) 1-564 F Cl H CF₃ CH₃ SCH₃ 1-565 F Cl H CF₃ CH₃ SC₂H₅1-566 F Cl H CF₃ CH₃ S^(i)C₃H₇ 1-567 F Cl H CF₃ CH₃ SCH₂CH₂Cl 1-568 F ClH CF₃ CH₃ S^(c)C₅H₉ 1-569 F Cl H CF₃ CH₃ S^(c)C₆H₁₁ 1-570 F Cl H CF₃ CH₃SCH₂CH═CH₂ 1-571 F Cl H CF₃ CH₃ SCH₂CCl═CH₂ 1-572 F Cl H CF₃ CH₃SCH₂CCl═CHCl 1-573 F Cl H CF₃ CH₃ SCH(CH₃)CH=CH₂ 1-574 F Cl H CF₃ CH₃SCH₂C≡CH 1-575 F Cl H CF₃ CH₃ SCH(CH₃)C≡CH 1-576 F Cl H CF₃ CH₃SCH₂COOCH₃ 1-577 F Cl H CF₃ CH₃ SCH₂COOC₂H₃ 1-578 F Cl H CF₃ CH₃SCH₂COO^(n)C₃H₇ 1-579 F Cl H CF₃ CH₃ SCH₂COO^(n)C₄H₉ 1-580 F Cl H CF₃CH₃ SCH₂COO^(n)C₅H₁₁ 1-581 F Cl H CF₃ CH₃ SCH₂COO^(i)C₃H₇ 1-582 F Cl HCF₃ CH₃ SCH₂COO^(c)C₅H₉ 1-583 F Cl H CF₃ CH₃ SCH₂COO^(c)C₆H₁₁ 1-584 F ClH CF₃ CH₃ SCH(CH₃)COOCH₃ 1-585 F Cl H CF₃ CH₃ SCH(CH₃)COOC₂H₅ 1-586 F ClH CF₃ CH₃ SCH(CH₃)COO^(n)C₃H₇ 1-587 F Cl H CF₃ CH₃ SCH(CH₃)COO^(n)C₄H₉1-588 F Cl H CF₃ CH₃ SCH(CH₃)COO^(n)C₅H₁₁ 1-589 F Cl H CF₃ CH₃SCH(CH₃)COO^(i)C₃H₇ 1-590 F Cl H CF₃ CH₃ SCH(CH₃)COO^(c)C₅H₉ 1-591 F ClH CF₃ CH₃ SCH(CH₃)COO^(c)C₆H₁₁ 1-592 F Cl H CF₃ CH₃ SCH₂CON(CH₃)₂ 1-593F Cl H CF₃ CH₃ SCH₂CON(C₂H₅)₂ 1-594 F Cl H CF₃ CH₃SCH₂CON(tetramethylene) 1-595 F Cl H CF₃ CH₃ SCH₂CON(pentamethylene)1-596 F Cl H CF₃ CH₃ SCH₂CON 1-597 F Cl H CF₃ CH₃ SCH(CH₃)CON(CH₃)₂1-598 F Cl H CF₃ CH₃ SCH(CH₃)CON(C₂H₅)₂ 1-599 F Cl H CF₃ CH₃ SCH(CH₃)CON(tetramethylene) 1-600 F Cl H CF₃ CH₃ SCH(CH_(3)CON) (pentamethylene)1-601 H F H CF₃ CH₃ SO₂Cl 1-602 H Cl H CF₃ CH₃ SO₂Cl 1-603 H Br H CF₃CH₃ SO₂Cl 1-604 F F H CF₃ CH₃ SO₂Cl 1-605 F Cl H CF₃ CH₃ SO₂Cl 1-606 FBr H CF₃ CH₃ SO₂Cl 1-607 H Cl H CF₃ CH₃ SO₂OCH₃ 1-608 H Cl H CF₃ CH₃SO₂OC₂H₅ 1-609 H Cl H CF₃ CH₃ SO₂O^(i)C₃H₇ 1-610 H Cl H CF₃ CH₃SO₂OCH₂CH═CH₂ 1-611 F Cl H CF₃ CH₃ SO₂OCH₃ 1-612 F Cl H CF₃ CH₃ SO₂OC₂H₅1-613 F Cl H CF₃ CH₃ SO₂O^(i)C₃H₇ 1-614 F Cl H CF₃ CH₃ SO₂OCH₂CH═CH₂1-615 H Cl H CF₃ CH₃ SO₂N(CH₃)₂ 1-616 H Cl H CF₃ CH₃ SO₂N(C₂H₅)₂ 1-617 FCl H CF₃ CH₃ SO₂N(CH₃)₂ 1-618 F Cl H CF₃ CH₂ SO₂N(C₂H₅)₂ 1-619 H Cl HCF₃ CH₃ COOH 1-620 H Cl H CF₃ CH₃ COOCH₃ 1-621 H Cl H CF₃ CH₃ COOC₂H₅1-622 H Cl H CF₃ CH₃ COO^(n)C₃H₇ 1-623 H Cl H CF₃ CH₃ COO^(n)C₄H₉ 1-624H Cl H CF₃ CH₃ COO^(n)C₅H₁₁ 1-625 H Cl H CF₃ CH₃ COO^(i)C₃H₃ 1-626 H ClH CF₃ CH₃ COOCH₂CH₂Cl 1-627 H Cl H CF₃ CH₃ COOCH₂CH₂Br 1-628 H Cl H CF₃CH₃ CON(CH₃)₂ 1-629 H Cl H CF₃ CH₃ CONHCH₃ 1-630 H Cl H CF₃ CH₃CON(C₂H₅)₂ 1-631 H Cl H CF₃ CH₃ CONHC₂H₅ 1-632 H Cl H CF₃ CH₃ COCH₃1-633 H Cl H CF₃ CH₃ COC₂H₅ 1-634 H Cl H CF₃ CH₃ COCH₂Cl 1-635 H Cl HCF₃ CH₃ CHO 1-636 H Cl H CF₃ CH₃ CH═CHCOOCH₃ 1-637 H Cl H CF₃ CH₃CH═CHCOOC₂H₅ 1-638 H Cl H CF₃ CH₃ CH₂CH₂COOCH₃ 1-639 H Cl H CF₃ CH₃CH₂CH₂COOC₂H₅ 1-640 F Cl H CF₃ CH₃ COOH 1-641 F Cl H CF₃ CH₃ COOCH₃1-642 F Cl H CF₃ CH₃ COOC₂H₃ 1-643 F Cl H CF₃ CH₃ COO^(n)C₃H₇ 1-644 F ClH CF₃ CH₃ COO^(n)C₄H₉ 1-645 F Cl H CF₃ CH₃ COO^(n)C₅H₁₁ 1-646 F Cl H CF₃CH₃ COO^(i)C₃H₇ 1-647 F Cl H CF₃ CH₃ COOCH₂CH₂Cl 1-648 F Cl H CF₃ CH₃COOCH₂CH₂Br 1-649 F Cl H CF₃ CH₃ CON(CH ₃)₂ 1-650 F Cl H CF₃ CH₃ CONHCH₃1-651 F Cl H CF₃ CH₃ CON(C₂H₅)₂ 1-652 F Cl H CF₃ CH₃ CONHC₂H₅ 1-653 F ClH CF₃ CH₃ COCH₃ 1-654 F Cl H CF₃ CH₃ COC₂H₃ 1-655 F Cl H CF₃ CH₃ COCH₂Cl1-656 F Cl H CF₃ CH₃ CHO 1-657 F Cl H CF₃ CH₃ CH═CHCOOCH₃ 1-658 F Cl HCF₃ CH₃ CH═CHCOOC₂H₅ 1-659 F Cl H CF₃ CH₃ CH₂CH₂COOCH₃ 1-660 F Cl HCF₂Cl CH₃ CH₂CH₂COOC₂H₅ 1-661 Cl Cl H CF₂Cl H H 1-662 H F H CF₂Cl H NO₂1-663 H Cl H CF₂Cl H NO₂ 1-664 H Br H CF₂Cl H NO₂ 1-665 F F H CF₂C1 HNO₂ 1-666 F Cl H CF₂Cl H NO₂ 1-667 F Br H CF₂Cl H NO₂ 1-668 H F H CF₂ClH NH₂ 1-669 H Cl H CF₂Cl H NH₂ 1-670 H Br H CF₂Cl H NH₂ 1-671 F F HCF₂Cl H NH₂ 1-672 F Cl H CF₂Cl H NH₂ 1-673 F Br H CF₂Cl H NH₂ 1-674 H FH CF₂Cl H OH 1-675 H Cl H CF₂Cl H OH 1-676 H Br H CF₂Cl H OH 1-677 F F HCF₂Cl H OH 1-678 F Cl H CF₂Cl H OH 1-679 F Br H CF₂C1 H OH 1-680 H Cl HCF₂Cl H NHCH₃ 1-681 H Cl H CF₂Cl H NHC₂H₃ 1-682 H Cl H CF₂Cl HNHCH₂CH═CH₂ 1-683 H Cl H CF₂Cl H NHCH₂C≡CH 1-684 H Cl H CF₂Cl HNHCH(CH₃)C≡CH 1-685 H Cl H CF₂Cl H NHSO₂CH₃ 1-686 H Cl H CF₂Cl HNHSO₂C₂H₅ 1-687 H Cl H CF₂Cl H NHSO₂CH₂Cl 1-688 H Cl H CF₂Cl H NHSO₂CF₃1-689 H Cl H CF₂Cl H N(CH₃)SO₂CH₃ 1-690 H Cl H CF₂Cl H N(CH₂C≡CH)SO₂CH₃1-691 H Cl H CF₂Cl H NHCOOCH₃ 1-692 H Cl H CF₂Cl H NHCOOC₂H₅ 1-693 H ClH CF₂Cl H NHCOO^(n)C₃H₇ 1-694 H Cl H CF₂Cl H NHCOO^(i)C₃H₇ 1-695 H Cl HCF₂Cl H NHCOO^(n)C₄H₉ 1-696 H Cl H CF₂Cl H NHCOO^(n)C₅H₁₁ 1-697 H Cl HCF₂Cl H NHCH₂COOCH₃ 1-698 H Cl H CF₂Cl H NHCH₂COOC₂H₃ 1-699 H Cl H CF₂ClH NHCH₂COO^(n)C₃H₇ 1-700 H Cl H CF₂Cl H NHCH₂COO^(n)C₄H₉ 1-701 H Cl HCF₂Cl H NHCH₂COO^(n)C₅H₁₁ 1-702 H Cl H CF₂Cl H NHCH₂COO^(i)C₃H₇ 1-703 HCl H CF₂Cl H NHCH₂COO^(c)C₅H₉ 1-704 H Cl H CF₂Cl H NHCH₂COO^(c)C₆H₁₁1-705 H Cl H CF₂Cl H NHCH(CH₃)COOCH₃ 1-706 H Cl H CF₂Cl HNHCH(CH₃)COOC₂H₃ 1-707 H Cl H CF₂Cl H NHCH(CH₃)COO^(n)C₃H₇ 1-708 H Cl HCF₂Cl H NHCH(CH₃)COO_(n)C₄H₉ 1-709 H Cl H CF₂Cl H NHCH(CH₃)COO^(n)C₅H₃1-710 H Cl H CF₂Cl H NHCH(CH₃)COO^(i)C₃H₇ 1-711 H Cl H CF₂Cl HNHCH(CH₃)COO^(c)C₅H₉ 1-712 H Cl H CF₂Cl H NHCH(CH₃)COO^(c)C₆H₁₁ 1-713 FCl H CF₂Cl H NHCH₃ 1-714 F Cl H CF₂C1 H NHC₂H₅ 1-715 F Cl H CF₂Cl HNHCH₂CH═CH₂ 1-716 F Cl H CF₂Cl H NHCH₂C≡CH 1-717 F Cl H CF₂Cl HNHCH(CH₃)C≡CH 1-718 F Cl H CF₂Cl H NHSO₂CH₃ 1-719 F Cl H CF₂Cl HNHSO₂C₂H₅ 1-720 F Cl H CF₂Cl H NHSO₂CH₂Cl 1-721 F Cl H CF₂Cl H NHSO₂CF₃1-722 F Cl H CF₂Cl H N(CH₃)SO₂CH₃ 1-723 F Cl H CF₂Cl H N(CH₂C≡CH)SO₂CH₃1-724 F Cl H CF₂Cl H NOCOOCH₃ 1-725 F Cl H CF₂Cl H NHCOOC₂H₅ 1-726 F ClH CF₂Cl H NHCOO^(n)C₃H₇ 1-727 F Cl H CF₂Cl H NHCOO^(i)C₃H₇ 1-728 F Cl HCF₂Cl H NHCOO^(n)C₄H₉ 1-729 F Cl H CF₂Cl H NHCOO^(n)C₅H₁₁ 1-730 F Cl HCF₂Cl H NHCH₂COOCH₃ 1-731 F Cl H CF₂Cl H NHCH₂COOC₂H₅ 1-732 F Cl H CF₂ClH NHCH₂COO^(n)C₃H₇ 1-733 F Cl H CF₂Cl H NHCH₂COO^(n)C₄H₉ 1-734 F Cl HCF₂Cl H NHCH₂COO^(n)C₅H₁₁ 1-735 F Cl H CF₂Cl H NHCH₂COO^(i)C₃H₇ 1-736 FCl H CF₂C1 H NHCH₂COO^(c)C₅H₉ 1-737 F Cl H CF₂Cl H NH₂CH₂COO^(c)C₆H₁₁1-738 F Cl H CF₂Cl H NHCH(CH₃)COOCH₃ 1-739 F Cl H CF₂Cl HNHCH(CH₃)COOC₂H₅ 1-740 F Cl H CF₂Cl H NHCH(CH₃)COO^(n)C₃H₇ 1-741 F Cl HCF₂Cl H NHCH(CH₃)COO^(n)C₄H₉ 1-742 F Cl H CF₂Cl H NHCH(CH₃)COO^(n)C₅H₁₁1-743 F Cl H CF₂Cl H NHCH(CH₃)COO^(i)C₃H₇ 1-744 F Cl H CF₂Cl HNHCH(CH₃)COO^(c)C₅H₉ 1-745 F Cl H CF₂Cl H NHCH(CH₃)COO^(c)C₆H₁₁ 1-746 HCl H CF₂Cl H OCH₃ 1-747 H Cl H CF₂Cl H OC₂H₅ 1-748 H Cl H CF₂Cl HO^(i)C₃H₇ 1-749 H Cl H CF₂Cl H O^(n)C₃H₇ 1-750 H Cl H CF₂Cl H OCH₂CH₂Cl1-751 H Cl H CF₂Cl H OCF₂CF₂H 1-752 H Cl H CF₂Cl H O^(c)C₅H₉ 1-753 H ClH CF₂Cl H O^(c)C₆H₁₁ 1-754 H Cl H CF₂Cl H OCH₂CH═CH₂ 1-755 H Cl H CF₂ClH OCH₂CCl═CH₂ 1-756 H Cl H CF₂Cl H OCH₂CCl═CHCl 1-757 H Cl H CF₂Cl HOCH(CH₃)CH═CH₂ 1-758 H Cl H CF₂Cl H OCH₂C≡CH 1-759 H Cl H CF₂Cl HOCH(CH₃)C≡CH 1-760 H Cl H CF₂Cl H OCH₂C≡CBr 1-761 H Cl H CF₂Cl HOCH₂C≡CCl 1-762 H Cl H CF₂Cl H OCH₂C≡CCH₂Cl 1-763 H Cl H CF₂Cl H OCH₂CN1-764 H Cl H CF₂Cl H OCH₂OCH₃ 1-765 H Cl H CF₂Cl H OCH₂OC₂H₅ 1-766 H ClH CF₂Cl H OCH₂SCH₃ 1-767 H Cl H CF₂Cl H OCH₂COOCH₃ 1-768 H Cl H CF₂Cl HOCH₂COOC₂H₃ 1-769 H Cl H CF₂Cl H OCH₂COO^(n)C₃H₇ 1-770 H Cl H CF₂Cl HOCH₂COO^(n)C₄H₉ 1-771 H Cl H CF₂Cl H OCH₂COO^(n)C₅H₁₁ 1-772 H Cl H CF₂ClH OCH₂COO^(i)C₃H₇ 1-773 H Cl H CF₂Cl H OCH₂COO^(c)C₅H₉ 1774 H Cl H CF₂ClH OCH₂COO^(c)C₆H₁₁ 1-775 H Cl H CF₂Cl H OCH(CH₃)COOCH₃ 1-776 H Cl HCF₂Cl H OCH(CH₃)COOC₂H₅ 1-777 H Cl H CF₂Cl H OCH(CH₃)COO^(n)C₃H₇ 1-778 HCl H CF₂Cl H OCH(CH₃)COO^(n)C₄H₉ 1-779 H Cl H CF₂Cl HOCH(CH₃)COO^(n)C₅H₁₁ 1-780 H Cl H CF₂Cl H OCH(CH₃)COO^(i)C₃H₇ 1-781 H ClH CF₂Cl H OCH(CH₃)COO^(c)C₅H₉ 1-782 H Cl H CF₂Cl H OCH(CH₃)COO^(c)C₆H₁₁1-783 H Ci H CF₂Cl H OCH₂CON(CH₃)₂ 1-784 H Cl H CF₂Cl H OCH₂CON(C₂H₅₎ ₂1-785 H Cl H CF₂Cl H OCH₂CON(CH₃)C₂H₅ 1-786 H Cl H CF₂Cl HOCH(CH₃)CON(CH₃)₂ 1-787 H Cl H CF₂Cl H OCH(CH₃)CON(C₂H₃ 1-788 H Cl HCF₂Cl H OCH(CH₃)CON(CH₃)C₂H₅ 1-789 H Cl H CF₂Cl H OCH₂COON(CH₃)₂ 1-790 HCl H CF₂Cl H OCH₂COON(C₂H₃ 1-791 H Cl H CF₂Cl H OCH(CH₃)COON(CH₃)₂ 1-792H Cl H CF₂Cl H OCH(CH₃)COON(C₂H₅₎ ₂ 1-793 F Cl H CF₂Cl H OCH₃ 1-794 F ClH CF₂Cl H OC₂H₃ I -795 F Cl H CF₂Cl H O^(i)C₃H₇ 1-796 F Cl H CF₂Cl HO^(n)C₃H₇ 1-797 F Cl H CF₂Cl H OCH₂CH₂Cl 1-798 F Cl H CF₂Cl H OCF₂CF₂H₅1-799 F Cl H CF₂Cl H O^(c)C₅H₉ 1-800 F Cl H CF₂Cl H O^(c)C₆H₁₁ 1-801 FCl H CF₂Cl H OCH₂CH═CH₂ 1-802 F Cl H CF₂Cl H OCH₂CCl═CH₂ 1-803 F Cl HCF₂Cl H OCH₂CCl═CHCl 1-804 F Cl H CF₂Cl H OCH(CH₃)CH═CH₂ 1-805 F Cl HCF₂Cl H OCH₂C≡CH 1-806 F Cl H CF₂Cl H OCH(CH₃)C≡CH 1-807 F Cl H CF₂Cl HOCH₂C≡CBr 1-808 F Cl H CF₂Cl H OCH₂C≡CCl 1-809 F Cl H CF₂Cl HOCH₂C≡CCH₂Cl 1-810 F Cl H CF₂Cl H OCH₂CN 1-811 F Cl H CF₂Cl H OCH₂OCH₃1-812 F Cl H CF₂Cl H OCH₂OC₂H₅ 1-813 F Cl H CF₂Cl H OCH₂SCH₃ 1-814 F ClH CF₂Cl H OCH₂COOCH₃ 1-815 F Cl H CF₂Cl H OCH₂COOC₂H₅ 1-816 F Cl H CF₂ClH OCH₂COO^(n)C₃H₇ 1-817 F Cl H CF₂Cl H OCH₂COO^(n)C₄H₉ 1-818 F Cl HCF₂Cl H OCH₂COO^(n)C₅H₁₁ 1-819 F Cl H CF₂Cl H OCH₂COO^(i)C₃H₇ 1-820 F ClH CF₂Cl H OCH₂COO^(c)C₅H₉ 1-821 F Cl H CF₂Cl H OCH₂COO^(c)C₆H₁₁ 1-822 FCl H CF₂Cl H OCH(CH₃)COOCH₃ 1-823 F Cl H CF₂Cl H OCH(CH₃)COOC₂H₅ 1-824 FCl H CF₂Cl H OCH(CH₃)COO^(n)C₃H₇ 1-825 F Cl H CF₂Cl HOCH(CH₃)COO^(n)C₄H₉ 1-826 F Cl H CF₂Cl H OCH(CH₃)COO^(n)C₅H₁₁ 1-827 F ClH CF₂Cl H OCH(CH₃)COO^(i)C₃H₇ 1-828 F Cl H CF₂Cl H OCH(CH₃)COO^(c)C₅H₉1-829 F Cl H CF₂Cl H OCH(CH 3)COO^(c)C₆H₁₁ 1-830 F Cl H CF₂Cl HOCH₂CON(CH₃)₂ 1-831 F Cl H CF₂Cl H OCH₂CON(C₂H₅)₂ 1-832 F Cl H CF₂Cl HOCH₂CON(CH₃)C₂H₅ 1-833 F Cl H CF₂Cl H OCH(CH₃)CON(CH₃)₂ 1-834 F Cl HCF₂Cl H OCH(CH₃)CON(C₂H₅)₂ 1-835 F Cl H CF₂Cl H OCH(CH₃)CON(CH₃)C₂H₃1-836 F Cl H CF₂Cl H OCH₂COON(CH₃)₂ 1-837 F Cl H CF₂Cl H OCH₂COON(C₂H₅)1-838 F Cl H CF₂Cl H OCH(CH₃)COON(CH₃)₂ 1-839 F Cl H CF₂Cl HOCH(CH₃)COON(C₂H₅)₂ 1-840 H F H CF₂Cl H SH 1-841 H Cl H CF₂Cl H SH 1-842H Br H CF₂Cl H SH 1-843 F F H CF₂Cl H SH 1-844 F Cl H CF₂Cl H SH 1-845 FBr H CF₂Cl H SH 1-846 H Cl H CF₂Cl H SCH₃ 1-847 H Cl H CF₂Cl H SC₂H₅1-848 H Cl H CF₂Cl H S^(i)C₃H₇ 1-849 H Cl H CF₂Cl H SCH₂CH₂Cl 1-850 H ClH CF₂Cl H S^(c)C₅H₉ 1-851 H Cl H CF₂Cl H S^(c)C₆H₁₁ 1-852 H Cl H CF₂Cl HSCH₂CH═CH₂ 1-853 H Cl H CF₂Cl H SCH₂CCl═CH₂ 1-854 H Cl H CF₂Cl HSCH₂CCl═CHCl 1-855 H Cl H CF₂Cl H SCH(CH₃)CH═CH₂ 1-856 H Cl H CF₂Cl HSCH₂C≡CH 1-857 H Cl H CF₂Cl H SCH(CH₃)C≡CH 1-858 H Cl H CF₂Cl HSCH₂COOCH₃ 1-859 H Cl H CF₂Cl H SCH₂COOC₂H₃ 1-860 H Cl H CF₂Cl HSCH₂COO^(n)C₃H₇ 1-861 H Cl H CF₂Cl H SCH₂COO^(n)C₄H₉ 1-862 H Cl H CF₂ClH SCH₂COO^(n)C₅H₁₁ 1-863 H Cl H CF₂Cl H SCH₂COO^(i)C₃H₇ 1-864 H Cl HCF₂Cl H SCH₂COO^(c)C₅H₉ 1-865 H Cl H CF₂Cl H SCH₂COO^(c)C₆H₁₁ 1-866 H ClH CF₂Cl H SCH(CH₃)COOCH₃ 1-867 H Cl H CF₂Cl H SCH(CH₃)COOC₂H₅ 1-868 H ClH CF₂Cl H SCH(CH₃)COO^(n)C₃H₇ 1-869 H Cl H CF₂Cl H SCH(CH₃)COO^(n)C₄H₉1-870 H Cl H CF₂Cl H SCH(CH₃)COO^(n)C₅H₁₁ 1-871 H Cl H CF₂Cl HSCH(CH₃)COO^(i)C₃H₇ 1-872 H Cl H CF₂Cl H SCH(CH₃)COO^(c)C₅H₉ 1-873 H ClH CF₂Cl H SCH(CH₃)COO^(c)C₆H₁₁ 1-874 H Cl H CF₂Cl H SCH₂CON(CH₃)₂ 1-875H Cl H CF₂Cl H SCH₂CON(C₂H₅)₂ 1-876 H Cl H CF₂Cl HSCH₂CON(tetramethylene) 1-877 H Cl H CF₂Cl H SCH₂CON(pentamethylene)1-878 H Cl H CF₂Cl H SCH₂CON (ethyleneoxyethylene) 1-879 H Cl H CF₂Cl HSCH(CH₃)CON(CH₃)₂ 1-880 H Cl H CF₂Cl H SCH(CH₃)CON(C₂H₅)₂ 1-881 H Cl HCF₂Cl H SCH(CH₃)CON (tetramethylene) 1-882 H Cl H CF₂Cl H SCH(CH₃)CON(pentamethylene) 1-883 F Cl H CF₂Cl H SCH₃ 1-884 F Cl H CF₂Cl H SC₂H₅1-885 F Cl H CF₂Cl H S^(i)C₃H₇ 1-886 F Cl H CF₂Cl H SCH₂CH₂Cl 1-887 F ClH CF₂Cl H S^(c)C₅H₉ 1-888 F Cl H CF₂Cl H S^(c)C₆H₁₁ 1-889 F Cl H CF₂Cl HSCH₂CH═CH₂ 1-890 F Cl H CF₂Cl H SCH₂CCl═CH₂ 1-891 F Cl H CF₂Cl HSCH₂CCl═CHCl 1-892 F Cl H CF₂Cl H SCH(CH₃)CH═CH₂ 1-893 F Cl H CF₂Cl HSCH₂C≡CH 1-894 F Cl H CF₂Cl H SCH(CH₃)C≡CH 1-895 F Cl H CF₂Cl HSCH₂COOCH₃ 1-896 F Cl H CF₂Cl H SCH₂COOC₂H₃ 1-897 F Cl H CF₂Cl HSCH₂COO^(n)C₃H₇ 1-898 F Cl H CF₂Cl H SCH₂COO^(n)C₄H₉ 1-899 F Cl H CF₂ClH SCH₂COO^(n)C₅H₁₁ 1-900 F Cl H CF₂Cl H SCH₂COO^(i)C₃H₇ 1-901 F Cl HCF₂Cl H SCH₂COO^(c)C₅H₉ 1-902 F Cl H CF₂Cl H SCH₂COO^(c)C₆H₁₁ 1-903 F ClH CF₂Cl H SCH(CH₃)COOCH₃ 1-904 F Cl H CF₂Cl H SCH(CH₃)COOC₂H₅ 1-905 F ClH CF₂Cl H SCH(CH₃)COO^(n)C₃H₇ 1-906 F Cl H CF₂Cl H SCH(CH₃)COO^(n)C₄H₉1-907 F Cl H CF₂Cl H SCH(CH₃)COO^(n)C₅5 H₁₁ 1-908 F Cl H CF₂Cl HSCH(CH₃)COO^(i)C₃H₇ 1-909 F Cl H CF₂Cl H SCH(CH₃)COO^(c)C₅H₉ 1-910 F ClH CF₂Cl H SCH(CH₃)COO^(c)C₆H₁₁ 1-911 F Cl H CF₂Cl H SCH₂CON(CH₃)₂ 1-912F Cl H CF₂Cl H SCH₂CON(C₂H₅)₂ 1-913 F Cl H CF₂Cl HSCH₂CON(tetramethylene) 1-914 F Cl H CF₂Cl H SCH₂CON(pentamethylene)1-915 F Cl H CF₂Cl H SCH₂CON (ethyleneoxyethylene) 1-916 F Cl H CF₂Cl HSCH(CH₃)CON(CH₃)₂ 1-917 F Cl H CF₂Cl H SCH(CH₃)CON(C₂H₅)₂ 1-918 F Cl HCF₂Cl H SCH(CH₃)CON (tetramethylene) 1-919 F Cl H CF₂Cl H SCH(CH₃)CON(pentamethylene) 1-920 H F H CF₂Cl H SO₂Cl 1-921 H Cl H CF₂Cl H SO₂Cl1-922 H Br H CF₂Cl H SO₂Cl 1-923 F F H CF₂Cl H SO₂Cl 1-924 F Cl H CF₂ClH SO₂Cl 1-925 F Br H CF₂Cl H SO₂Cl 1-926 H Cl H CF₂Cl H SO₂OCH₃ 1-927 HCl H CF₂Cl H SO₂OC₂H₅ 1-928 H Cl H CF₂Cl H SO₂O^(i)C₃H₇ 1-929 H Cl HCF₂Cl H SO₂OCH₂CH═CH₂ 1-930 F Cl H CF₂Cl H SO₂OCH₃ 1-931 F Cl H CF₂Cl HSO₂OC₂H₅ 1-932 F Cl H CF₂Cl H SO₂O^(i)C₃H₇ 1-933 F Cl H CF₂Cl HSO₂OCH₂CH═CH₂ 1-934 H Cl H CF₂Cl H SO₂N(CH₃)₂ 1-935 H Cl H CF₂Cl HSO₂N(C₂H₅)₂ 1-936 F Cl H CF₂Cl H SO₂N(CH₃)₂ 1-937 F Cl H CF₂Cl HSO₂N(C₂H₅)₂ 1-938 H Cl H CF₂Cl H COOH 1-939 H Cl H CF₂Cl H COOCH₃ 1-940H Cl H CF₂Cl H COOC₂H₅ 1-941 H Cl H CF₂Cl H COO^(n)C₃H₇ 1-942 H Cl HCF₂Cl H COO^(n)C₄H₉ 1-943 H Cl H CF₂Cl H COO^(n)C₅H₁₁ 1-944 H Cl H CF₂ClH COO^(i)C₃H₇ 1-945 H Cl H CF₂Cl H COOCH₂CH₂Cl 1-946 H Cl H CF₂Cl HCOOCH₂CH₂Br 1-947 H Cl H CF₂Cl H CON(CH₃)₂ 1-948 H Cl H CF₂Cl H CONHCH₃1-949 H Cl H CF₂Cl H CON(C₂H₅)₂ 1-950 H Cl H CF₂Cl H CONHC₂H₅ 1-951 H ClH CF₂Cl H COCH₃ 1-952 H Cl H CF₂Cl H COC₂H₅ 1-953 H Cl H CF₂Cl H COCH₂Cl1-954 H Cl H CF₂Cl H CHO 1-955 H Cl H CF₂Cl H CH═CHCOOCH₃ 1-956 H Cl HCF₂Cl H CH═CHCOOC₂H₅ 1-957 H Cl H CF₂Cl H CH₂CH₂COOCH₃ 1-958 H Cl HCF₂Cl H CH₂CH₂COOC₂H₅ 1-959 F Cl H CF₂Cl H COOH 1-960 F Cl H CF₂Cl HCOOCH₃ 1-961 F Cl H CF₂Cl H COOC₂H₅ 1-962 F Cl H CF₂Cl H COO^(n)C₃H₇1-963 F Cl H CF₂Cl H COO^(n)C₄H₉ 1-964 F Cl H CF₂Cl H COO^(n)C₅H₁₁ 1-965F Cl H CF₂Cl H COO^(i)C₃H₇ 1-966 F Cl H CF₂Cl H COOCH₂CH₂Cl 1-967 F Cl HCF₂Cl H COOCH₂CH₂Br 1-968 F Cl H CF₂Cl H CON(CH₃)₂ 1-969 F Cl H CF₂Cl HCONHCH₃ 1-970 F Cl H CF₂Cl H CON(C₂H₅)₃ 1-971 F Cl H CF₂Cl H CONHC₂H₅1-972 F Cl H CF₂Cl H COCH₃ 1-973 F Cl H CF₂Cl H COC₂H₅ 1-974 F Cl HCF₂Cl H COCH₂Cl 1-975 F Cl H CF₂Cl H CHO 1-976 F Cl H CF₂Cl HCH═CHCOOCH₃ 1-977 F Cl H CF₂Cl H CH═CHCOOC₂H₅ 1-978 F Cl H CF₂Cl HCH₂CH₂COOCH₃ 1-979 F Cl H CF₂Cl H CH₂CH₂COOC₂H₅ 1-980 H F H CF₃ H NO₂1-981 H Cl H CF₃ H NO₂ 1-982 H Br H CF₃ H NO₂ 1-983 F F H CF₃ H NO₂1-984 F Cl H CF₃ H NO₂ 1-985 F Br H CF₃ H NO₂ 1-986 H F H CF₃ H NH₂1-987 H Cl H CF₃ H NH₂ 1-988 H Br H CF₃ H NH₂ 1-989 F F H CF₃ H NH₂1-990 F Cl H CF₃ H NH₂ 1-991 H Cl H CF₃ H NHCH(CH₃)COOCH₃ 1-992 H Cl HCF₃ H NHCH(CH₃)COOC₂H₅ 1-993 H Cl H CF₃ H NHCH(CH₃)COO^(n)C₃H₇ 1-994 HCl H CF₃ H NHCH(CH₃)COO^(n)C₄H₉ 1-995 H Cl H CF₃ H NHCH(CH₃)COO^(n)C₅H₁₁1-996 H Cl H CF₃ H NHCH(CH₃)COO^(i)C₃H₇ 1-997 H Cl H CF₃ HNHCH(CH₃)COO^(c)C₅H₉ 1-998 H Cl H CF₃ H NHCH(CH₃)COO^(c)C₆H₁₁ 1-999 F ClH CF₃ H NHCH₃ 1-1000 F Cl H CF₃ H NHC₂H₅ 1-1001 F Cl H CF₃ H NHCH₂CH═CH₂1-1002 F Cl H CF₃ H NHCH₂C≡CH 1-1003 F Cl H CF₃ H NHCH(CH₃)C≡CH 1-1004 FCl H CF₃ H NHSO₂CH₃ 1-1005 F Cl H CF₃ H NHSO₂C₂H₅ 1-1006 F Cl H CF₃ HNHSO₂CO₂Cl 1-1001 F Cl H CF₃ H NHSO₂CF₃ 1-1008 F Cl H CF₃ H N(CH₃)SO₂CH₃1-1009 F Cl H CF₃ H N(CH₂C≡CH)SO₂CH₃ 1-1010 F Cl H CF₃ H NHCOOCH₃ 1-1011F Cl H CF₃ H NHCOOC₂H₅ 1-1012 F Cl H CF₃ H NHCOO^(n)C₃H₇ 1-1013 F Cl HCF₃ H NHCOO^(i)C₃H₇ 1-1014 F Cl H CF₃ H NHCOO^(n)C₄H₉ 1-1015 F Cl H CF₃H NHCOO^(n)C₅H₁₁ 1-1016 F Cl H CF₃ H NHCH₂COOCH₃ 1-1017 F Cl H CF₃ HNHCH₂COOC₂H₅ 1-1018 F Cl H CF₃ H NHCH₂COO^(n)C₃H₇ 1-1019 F Cl H CF₃ HNHCH₂COO^(n)C₄H₉ 1-1020 F Cl H CF₃ H NHCH₂COO^(n)C₅H₁₁ 1-1021 F Cl H CF₃H NHCH₂COO^(i)C₃H₇ 1-1022 F Cl H CF₃ H NHCH₂COO^(c)C₅H₉ 1-1023 F Br HCF₃ H NH₂ 1-1024 H F H CF₃ H OH 1-1025 H Cl H CF₃ H OH 1-1026 H Br H CF₃H OH 1-1027 F F H CF₃ H OH 1-1028 F Cl H CF₃ H OH 1-1029 F Br H CF₃ H OH1-1030 H Cl H CF₃ H NHCH₃ 1-1031 H Cl H CF₃ H NHC₂H₅ 1-1032 H Cl H CF₃ HNHCH₂CH═CH₂ 1-1033 H Cl H CF₃ H NHCH₂C≡CH 1-1034 H Cl H CF₃ HNHCH(CH₃)C≡CH 1-1035 H Cl H CF₃ H NHSO₂CH₃ 1-1036 H Cl H CF₃ H NHSO₂C₂H₅1-1037 H Cl H CF₃ H NHSO₂CH₂Cl 1-1038 H Cl H CF₃ H NHSO₂CF₃ 1-1039 H ClH CF₃ H N(CH₃)SO₂CH₃ 1-1040 H Cl H CF₃ H N(CH₂C≡CH)SO₂CH₃ 1-1041 H Cl HCF₃ H NHCOOCH₃ 1-1042 H Cl H CF₃ H NHCOOC₂H₅ 1-1043 H Cl H CF₃ HNHCOO^(n)C₃H₇ 1-1044 H Cl H CF₃ H NHCOO^(i)C₃H₇ 1-1045 H Cl H CF₃ HNHCOO^(n)C₄H₉ 1-1046 H Cl H CF₃ H NHCOO^(n)C₅H₁₁ 1-1047 H Cl H CF₃ HNHCH₂COOCH₃ 1-1048 H Cl H CF₃ H NHCH₂COOC₂H₅ 1-1049 H Cl H CF₃ HNHCH₂COO^(n)C₃H₇ 1-1050 H Cl H CF₃ H NHCH₂COO^(n)C₄H₉ 1-1051 H Cl H CF₃H NHCH₂COO^(n)C₅H₁₁ 1-1052 H Cl H CF₃ H NHCH₂COO^(i)C₃H₇ 1-1053 H Cl HCF₃ H NHCH₂COO^(c)C₅H₉ 1-1054 H Cl H CF₃ H NHCH₂COO^(c)C₆H₁₁ 1-1055 F ClH CF₃ H NH CH₂COO^(c)C₆H₁₁ 1-1056 F Cl H CF₃ H NHCH(CH₃)COOCH₃ 1-1057 FCl H CF₃ H NHCH(CH₃)COOC₂H₅ 1-1058 F Cl H CF₃ H NHCH(CH₃)COO^(n)C₃H₇1-1059 F Cl H CF₃ H NHCH(CH₃)COO^(n)C₄H₉ 1-1060 F Cl H CF₃ HNHCH(CH₃)COO^(n)C₅H₁₁ 1-1061 F Cl H CF₃ H NHCH(CH₃)COO^(i)C₃H₇ 1-1062 FCl H CF₃ H NHCH(CH₃)COO^(c)C₅H₉ 1-1063 F Cl H CF₃ HNHCH(CH₃)COO^(c)C₆H₁₁ 1-1064 H Cl H CF₃ H OCH₃ 1-1065 H Cl H CF₃ H OC₂H₅1-1066 H Cl H CF₃ H O^(i)C₃H₇ 1-1067 H Cl H CF₃ H O^(n)C₃H₇ 1-1068 H ClH CF₃ H OCH₂CH₂Cl 1-1069 H Cl H CF₃ H OCF_(2 CF) ₂H 1-1070 H Cl H CF₃ HO^(c)C₅H₉ 1-1071 H Cl H CF₃ H O^(c)C₆H₁₁ 1-1072 H Cl H CF₃ H OCH₂CH═CH₂1-1073 H Cl H CF₃ H OCH₂CCl═CH₂ 1-1074 H Cl H CF₃ H OCH₂CCl═CHCl 1-1075H Cl H CF₃ H OCH(CH₃)CH═CH₂ 1-1076 H Cl H CF₃ H OCH₂C≡CH 1-1077 H Cl HCF₃ H OCH(CH₃)C≡CH 1-1078 H Cl H CF₃ H OCH₂C≡CBr 1-1079 H Cl H CF₃ HOCH₂C≡CCl 1-1080 H Cl H CF₃ H OCH₂C≡CCH₂Cl 1-1081 H Cl H CF₃ H OCH₂CN1-1082 H Cl H CF₃ H OCH₂OCH₃ 1-1083 H Cl H CF₃ H OCH₂OC₂H₃ 1-1084 H Cl HCF₃ H OCH₂SCH₃ 1-1085 H Cl H CF₃ H OCH₂COOCH₃ 1-1086 H Cl H CF₃ HOCH₂COOC₂H₅ 1-1087 H Cl H CF₃ H OCH₂COO^(n)C₃H₇ 1-1088 H Cl H CF₃ HOCH₂COO^(n)C₄H₉ 1-1089 H Cl H CF₃ H OCH₂COO^(n)C₅H₁₁ 1-1090 H Cl H CF₃ HOCH₂COO^(i)C₃H₇ 1-1091 H Cl H CF₃ H OCH₂COO^(c)C₅H₉ 1-1092 H Cl H CF₃ HOCH₂COO^(c)C₆H₁₁ 1-1093 H Cl H CF₃ H OCH(CH₃)COOCH₃ 1-1094 H Cl H CF₃ HOCH(CH₃)COOC₂H₅ 1-1095 H Cl H CF₃ H OCH(CH₃)COO^(n)C₃H₇ 1-1096 H Cl HCF₃ H OCH(CH₃)COO^(n)C₄H₉ 1-1097 H Cl H CF₃ H OCH(CH₃)COO^(n)C₅H₁₁1-1098 H Cl H CF₃ H OCH(CH₃)COO^(i)C₃H₇ 1-1099 H Cl H CF₃ HOCH(CH₃)COO^(c)C₅H₉ 1-1100 H Cl H CF₃ H OCH(CH₃)COO^(c)C₆H₁₁ 1-1101 H ClH CF₃ H OCH₂CON(CH₃)₂ 1-1102 H Cl H CF₃ H OCH₂CON(C₂H₅)₂ ~ -1103 H Cl HCF₃ H OCH₂CON(CH₃)C₂H₅ 1-1104 H Cl H CF₃ H OCH(CH₃)CON(CH₃)₂ 1-1105 H ClH CF₃ H OCH(CH₃)CON(C₂H₅ 1-1106 H Cl H CF₃ H OCH(CH₃)CON(CH₃)C₂H₅ 1-1107H Cl H CF₃ H OCH₂COON(CH₃)₂ 1-1108 H Cl H CF₃ H OCH₂COON(C₂H₅)₂ 1-1109 HCl H CF₃ H OCH(CH₃)COON(CH₃)₂ 1-1110 H Cl H CF₃ H OCH(CH₃)COON(C₂H₅)₂1-1111 F Cl H CF₃ H OCH₃ 1-1112 F Cl H CF₃ H OC₂H₅ 1-1113 F Cl H CF₃ HO^(i)C₃H₇ 1-1114 F Cl H CF₃ H O^(n)C₃H₇ 1-1115 F Cl H CF₃ H OCH₂CH₂Cl1-1116 F Cl H CF₃ H OCF₂CF₂H 1-1117 F Cl H CF₃ H O^(c)C₅H₉ 1-1118 F Cl HCF₃ H O^(c)C₆H₁₁ 1-1119 F Cl H CF₃ H OCH₂CH═CH₂ 1-1120 F Cl H CF₃ HOCH₂CCl═CH₂ 1-1121 F Cl H CF₃ H OCH₂CCl═CHCl 1-1122 F Cl H CF₃ HOCH(CH₃)CH═CH₂ 1--1123 F Cl H CF₃ H OCH₂C≡CH 1-1124 F Cl H CF₃ HOCH(CH₃)C≡CH 1-1125 F Cl H CF₃ H OCH₂C≡CBr 1-1126 F Cl H CF₃ H OCH₂C≡CCl1-1127 F Cl H CF₃ H OCH₂C≡CCH₂Cl 1-1128 F Cl H CF₃ H OCH₂CN 1-1129 F ClH CF₃ H OCH₂OCH₃ 1-1130 F Cl H CF₃ H OCH₂OC₂H₅ 1-1131 F Cl H CF₃ HOCH₂SCH₃ 1-1132 F Cl H CF₃ H OCH₂COOCH₃ 1-1133 F Cl H CF₃ H OCH₂COOC₂H₅1-1134 F Cl H CF₃ H OCH₂COO^(n)C₃H₇ 1-1135 F Cl H CF₃ H OCH₂COO^(n)C₄H₉1-1136 F Cl H CF₃ H OCH₂COO^(n)C₅H₁₁ 1-1137 F Cl H CF₃ H OCH₂COO^(i)C₃H₇1-1138 F Cl H CF₃ H OCH₂COO^(c)C₅H₉ 1-1139 F Cl H CF₃ H OCH₂COO^(c)C₆H₁₁1-1140 F Cl H CF₃ H OCH(CH₃)COOCH₃ 1-1141 F Cl H CF₃ H OCH(CH₃)COOC₂H₅1-1142 F Cl H CF₃ H OCH(CH₃)COO^(n)C₃H₇ 1-1143 F Cl H CF₃ HOCH(CH₃)COO^(n)C₄H₉ 1-1144 F Cl H CF₃ H OCH(CH₃)COO^(n)C₆H₁₁ 1-1145 F ClH CF₃ H OCH(CH₃)COO^(i)C₃H₇ 1-1146 F Cl H CF₃ H OCH(CH₃)COO^(c)C₅H₉1-1147 F Cl H CF₃ H OCH(CH₃)COO^(c)C₆H₁₁ 1-1148 F Cl H CF₃ HOCH₂CON(CH₃)₂ 1-1149 F Cl H CF₃ H OCH₂CON(C₂H₅)₂ 1-1150 F Cl H CF₃ HOCH₂CON(CH₃)C₂H₅ 1-1151 F Cl H CF₃ H OCH(CH₃)CON(CH₃)₂ 1-1152 F Cl H CF₃H OCH(CH₃)CON(C₂H₅)₂ 1-1153 F Cl H CF₃ H OCH(CH₃)CON(CH₃)C₂H₅ 1-1154 FCl H CF₃ H OCH₂COON(CH₃)₂ I -1155 F Cl H CF₃ H OCH₂COON(C₂H₅)₂ 1-1156 FCl H CF₃ H OCH(CH₃)COON(CH₃)₂ 1-1157 F Cl H CF₃ H OCH(CH₃)COON(C₂H₅)₂1-1158 H F H CF₃ H SH 1-1159 H Cl H CF₃ H SH 1-1160 H Br H CF₃ H SH1-1161 F F H CF₃ H SH 1-1162 F Cl H CF₃ H SH 1-1163 F Br H CF₃ H SH1-1164 H Cl H CF₃ H SCH₃ 1-1165 H Cl H CF₃ H SC₂H₅ 1-1166 H Cl H CF₃ HS^(i)C₃H₇ 1-1167 H Cl H CF₃ H SCH₂CH₂Cl 1-1168 H Cl H CF₃ H S^(c)C₅H₉1-1169 H Cl H CF₃ H S^(c)C₆H₁₁ 1-1170 H Cl H CF₃ H SCH₂CH═CH₂ 1-1171 HCl H CF₃ H SCH₂ CCl═CH₂ 1-1172 H Cl H CF₃ H SCH₂CCl═CHCl 1-1173 H Cl HCF₃ H SCH(CH₃)CH═CH₂ 1-1174 H Cl H CF₃ H SCH₂C≡CH 1-1175 H Cl H CF₃ HSCH(CH₃)C≡CH 1-1176 H Cl H CF₃ H SCH₂COOCH₃ 1-1177 H Cl H CF₃ HSCH₂COOC₂H₅ 1-1178 H Cl H CF₃ H SCH₂COO^(n)C₃H₇ 1-1179 H Cl H CF₃ HSCH₂COO^(n)C₄H₉ 1-1180 H Cl H CF₃ H SCH₂COO^(n)C₅H₁₁ 1-1181 H Cl H CF₃ HSCH₂COO^(i)C₃H₇ 1-1182 H Cl H CF₃ H SCH₂COO^(c)C₅H₉ 1-1183 H Cl H CF₃ HSCH₂COO^(c)C₆H₁₁ 1-1184 H Cl H CF₃ H SCH(CH₃)COOCH₃ 1-1185 H Cl H CF₃ HSCH(CH₃)COOC₂H₅ 1-1186 H Cl H CF₃ H SCH(CH₃)COO^(n)C₃H₇ 1-1187 H Cl HCF₃ H SCH(CH₃)COO^(n)C₄H₉ 1-1188 H Cl H CF₃ H SCH(CH₃)COO^(n)C₅H₁₁1-1189 H Cl H CF₃ H SCH(CH₃)COO^(i)C₃H₇ 1-1190 H Cl H CF₃ HSCH(CH₃)COO^(c)C₅H₉ 1-1191 H Cl H CF₃ H SCH(CH₃)COO^(c)C⁶H₁₁ 1-1192 H ClH CF₃ H SCH₂CON(CH₃)₂ 1-1193 H Cl H CF₃ H SCH₂CON(C₂H₅)₂ 1-1194 H Cl HCF₃ H SCH₂CON(tetramethylene) 1-1195 H Cl H CF₃ HSCH₂CON(pentamethylene) 1-1196 H Cl H CF₃ H SCH₂CON(ethyleneoxyethylene) 1-1197 H Cl H CF₃ H SCH(CH₃)CON(CH₃)₂ 1-1198 H ClH CF₃ H SCH(CH₃)CON(C₂H₅)₂ 1-1199 H Cl H CF₃ H SCH(CH₃)CON(tetramethylene) 1-1200 H Cl H CF₃ H SCH(CH₃)CON (pentamethylene) 1-1201F Cl H CF₃ H SCH₃ 1-1202 F Cl H CF₃ H SC₂H₅ 1-1203 F Cl H CF₃ HS^(i)C₃H₇ 1-1204 F Cl H CF₃ H SCH₂CH₂Cl 1-1205 F Cl H CF₃ H S^(c)C₅H₉1-1206 F Cl H CF₃ H S^(c)C₆H₁₁ 1-1207 F Cl H CF₃ H SCH₂CH═CH₂ 1-1208 FCl H CF₃ H SCH₂CCl═CH₂ 1-1209 F Cl H CF₃ H SCH₂CCl═CHCl 1-1210 F ~Cl HCF₃ H SCH(CH₃)CH═CH₂ 1-1211 F Cl H CF₃ H SCH₂C≡CH 1-1212 F Cl H CF₃ HSCH(CH₃)C≡CH 1-1213 F Cl H CF₃ H SCH₂COOCH₃ 1-1214 F Cl H CF₃ HSCH₂COOC₂H₅ 1-1215 F Cl H CF₃ H SCH₂COO^(n)C₃H₇ 1-1216 F Cl H CF₃ HSCH₂COO^(n)C₄H₉ 1-1217 F Cl H CF₃ H SCH₂COO^(n)C₅H₁₁ 1-1218 F Cl H CF₃ HSCH₂COO^(i)C₃H₇ 1-1219 F Cl H CF₃ H SCH₂COO_(c)C₅H₉ 1-1220 F Cl H CF₃ HSCH₂COO_(c)C₆H₁₁ 1-1221 F Cl H CF₃ H SCH(CH₃)COOCH₃ 1-1222 F Cl H CF₃ HSCH(CH₃)COOC₂H₆ 1-1223 F Cl H CF₃ H SCH(CH₃)COO^(n)C₃H₇ 1-1224 F Cl HCF₃ H SCH(CH₃)COO^(n)C₄H₉ 1-1225 F Cl H CF₃ H SCH(CH₃)COO^(n)C₅H₁₁1-1226 F Cl H CF₃ H SCH(CH₃)COO^(i)C₃H₇ 1-1227 F Cl H CF₃ HSCH(CH₃)COO^(c)C₅H₉ 1-1228 F Cl H CF₃ H SCH(CH₃)COO^(c)C₆H₁₁ 1-1229 F ClH CF₃ H SCH₂CON(CH₃)₂ 1-1230 F Cl H CF₃ H SCH₂CON(C₂H₅)₂ 1-1231 F Cl HCF₃ H SCH₂CON(tetramethylene) 1-1232 F Cl H CF₃ HSCH₂CON(pentamethylene) 1-1233 F Cl H CF₃ H SCH₂CON(ethyleneoxyethylene) 1-1234 F Cl H CF₃ H SCH(CH₃)CON(CH₃)₂ 1-1235 F ClH CF₃ H SCH(CH₃)CON(C₂H₅)₂ 1-1236 F Cl H CF₃ H SCH(CH₃)CON(tetramethylene) 1-1237 F Cl H CF₃ H SCH(CH₃)CON (pentamethylene) 1-1238H F H CF₃ H SO₂Cl 1-1239 H Cl H CF₃ H SO₂Cl 1-1240 H Br H CF₃ H SO₂Cl1-1241 F F H CF₃ H SO₂Cl 1-1242 F Cl H CF₃ H SO₂Cl 1-1243 F Br H CF₃ HSO₂Cl 1-1244 H Cl H CF₃ H SO₂OCH₃ 1-1245 H Cl H CF₃ H SO₂OC₂H₅ 1-1246 HCl H CF₃ H SO₂O^(i)C₃H₇ 1-1247 H Cl H CF₃ H SO₂OCH₂CH═CH₂ 1-1248 F Cl HCF₃ H SO₂OCH₃ 1-1249 F Cl H CF₃ H SO₂OC₂H₅ 1-1250 F Cl H CF₃ HSO₂O^(i)C₃H₇ 1-1251 F Cl H CF₃ H SO₂OCH₂CH═CH₂ 1-1252 H Cl H CF₃ HSO₂N(CH₃)₂ 1-1253 H Cl H CF₃ H SO₂N(C₂H₅)₂ 1-1254 F Cl H CF₃ H SO₂N(CH3)₂ 1-1255 F Cl H CF₃ H SO₂N(C₂H₅)₃ 1-1256 H Cl H CF₃ H COOH 1-1257 H ClH CF₃ H COOCH₃ 1-1258 H Cl H CF₃ H COOC₂H₅ 1-1259 H Cl H CF₃ HCOO^(n)C₃H₇ 1-1260 H Cl H CF₃ H COO^(n)C₄H₉ 1-1261 H Cl H CF₃ HCOO^(n)C₅H₁₁ 1-1262 H Cl H CF₃ H COO^(i)C₃H₇ 1-1263 H Cl H CF₃ HCOOCH₂CH₂Cl 1-1264 H Cl H CF₃ H COOCH₂CH₂Br 1-1265 H Cl H CF₃ HCON(CH₃)₂ 1-1266 H Cl H CF₃ H CONHCH₃ 1-1267 H Cl H CF₃ H CON(C₂H₅)₂1-1268 H Cl H CF₃ H CONHC₂H₅ 1-1269 H Cl H CF₃ H COCH₃ 1-1270 H Cl H CF₃H COC₂H₅ 1-1271 H Cl H CF₃ H COCH₂Cl 1-1272 H Cl H CF₃ H CHO 1-1273 H ClH CF₃ H CH═CHCOOCH₃ 1-1274 H Cl H CF₃ H CH=CHCOOC₂H₅ 1-1275 H Cl H CF₃ HCH₂CH₂COOCH₃ 1-1276 H Cl H CF₃ H CH₂CH₂COOC₂H₅ 1-1277 F Cl H CF₃ H COOH1-1278 F Cl H CF₃ H COOCH₃ 1-1279 F Cl H CF₃ H COOC₂H₅ 1-1280 F Cl H CF₃H COO^(n)C₃H₇ 1-1281 F Cl H CF₃ H COO^(n)C₄H₉ 1-1282 F Cl H CF₂ HCOO^(n)C₅H₁₁ 1-1283 F Cl H CF₃ H COO^(i)C₃H₇ 1-1284 F Cl H CF₃ HCOOCH₂CH₂Cl 1-1285 F Cl H CF₃ H COOCH₂CH₂Br 1-1286 F Cl H CF₃ HCON(CH₃)₂ 1-1287 F Cl H CF₃ H CONHCH₃ 1-1288 F Cl H CF₃ H CON(C₂H₅)₂1-1289 F Cl H CF₃ H CONHC₂H₅ 1-1290 F Cl H CF₃ H COCH₃ 1-1291 F Cl H CF₃H COC₂H₅ 1-1292 F Cl H CF₃ H COCH₂Cl 1-1293 F Cl H Cl% H CHO 1-1294 F ClH CF₃ H CH═CHCOOCH₃ 1-1295 F Cl H CF₃ H CH═CHCOOC₂H₅ 1-1296 F Cl H CF₃ HCH₂CH₂COOCH₃ 1-1297 F Cl H CF₃ H CH₂CH₂COOC₂H₅ 1-1298 H F CH₃ CF₃ H NO₂1-1299 H Cl CH₃ CF₃ H NO₂ 1-1300 H Br CH₃ CF₃ H NO₂ 1-1301 F F CH₃ CF₃ HNO₂ 1-1302 F Cl CH₃ CF₃ H NO₂ 1-1303 F Br CH₃ CF₃ H NO₂ 1-1304 H F CH₃CF H NH₂ 1-1305 H Cl CH₃ CF₃ H NH₂ 1-1306 H Br CH₃ CF₃ H NH₂ 1-1307 F FCH₃ CF₃ H NH₂ 1-1308 F Cl CH₃ CF₃ H NH₂ 1-1309 H Cl CH₃ CF₃ HNHCH(CH₃)COOCH₃ 1-1310 H Ci CH₃ CF₃ H NHCH(CH₃)COOC₂H₅ 1-1311 H Cl CH₃CF₃ H NHCH(CH₃)COO^(n)C₃H₇ 1-1312 H Cl CH₃ CF₃ H NHCH(CH₃)COO^(n)C₄H₉1-1313 H Cl CH₃ CF₃ H NHCH(CH₃)COO^(n)C₅H₁₁ 1-1314 H Cl CH₃ CF₃ HNHCH(CH₃)COO^(i)C₃H₇ 1-1315 H Cl CH₃ CF₃ H NHCH(CH₃)COO^(c)C₅H₉ 1-1316 HCl CH₃ CF₃ H NHCH(CH₃)COO^(c)C₆H₁₁ 1-1317 F Cl CH₃ CF₃ H NHCH₃ 1-1318 FCl CH₃ CF₃ H NHC₂H₅ 1-1319 F Cl CH₃ CF₃ H NHCH₂CH═CH₂ 1-1320 F Cl CH₃CF₃ H NHCH₂C≡CH 1-1321 F Cl CH₃ CF₃ H NHCH(CH₃)C≡CH 1-1322 F Cl CH₃ CF₃H NHSO₂CH₃ 1-1323 F Cl CH₃ CF₃ H NHSO₂C₂H₅ 1-1324 F Cl CH₃ CF₃ HNHSO₂CH₂Cl 1-1325 F Cl CH₃ CF₃ H NHSO₂CF₃ 1-1326 F Cl CH₃ CF₃ HN(CH₃)SO₂CH₃ 1-1327 F Cl CH₃ CF₃ H N(CH₂C≡CH)SO₂CH₃ 1-1328 F Cl CH₃ CF₃H NHCOOCH₃ 1-1329 F Cl CH₃ CF₃ H NHCOOC₂H₅ 1-1330 F Cl CH₃ CF₃ HNHCOO^(n)C₃H₇ 1-1331 F Cl CH₃ CF₃ H NHCOO^(i)C₃H₇ 1-1332 F Cl CH₃ CF₃ HNHCOO^(n)C₄H₉ 1-1333 F Cl CH₃ CF₃ H NHCOO^(n)C₅H₁₁ 1-1334 F Cl CH₃ CF₃ HNHCH₂COOCH₃ 1-1335 F Cl CH₃ CF₃ H NHCH₂COOC₂H₅ 1-1336 F Cl CH₃ CF₃ HNHCH₂COO^(n)C₃H₇ 1-1337 F Cl CH₃ CF₃ H NHCH₂COO^(n)C₄H₉ 1-1338 F Cl CH₃CF₃ H NHCH₂COO^(n)C₅H₁₁ 1-1339 F Cl CH₃ CF₃ H NHCH₂COO^(i)C₃H₇ 1-1340 FCl CH₃ CF₃ H NHCH₂COO^(c)C₅H₉ 1-1341 F Br CH₃ CF₃ H NH₂ 1-1342 H F CH₃CF₃ H OH 1-1343 H Cl CH₃ CF₃ H OH 1-1344 H Br CH₃ CF₃ H OH 1-1345 F FCH₃ CF₃ H OH 1-1346 F Cl CH₃ CF₃ H OH 1-1347 F Br CH₃ CF₃ H OH 1-1348 HCl CH₃ CF₃ H NHCH₃ 1-1349 H Cl CH₃ CF₃ H NHC₂H₅ 1-1350 H Cl CH₃ CF₃ HNHCH₂CH═CH₂ 1-1351 H Cl CH₃ CF₃ H NHCH₂C≡CH 1-1352 H Cl CH₃ CF₃ HNHCH(CH₃)C≡CH 1-1353 H Cl CH₃ CF₃ H NHSO₂CH₃ 1-1354 H 01 CH₃ CF₃ HNHSO₂C₂H₅ 1-1355 H Cl CH₃ CF₃ H NHSO₂CH₂Cl 1-1356 H Cl CH₃ CF₃ HNHSO₂CF₃ 1-1357 H Cl CH₃ CF₃ H N(CH₃)SO_(2 CH) ₃ 1-1358 H Cl CH₃ CF₃ HN(CH₂C≡CH)SO₂CH₃ 1-1359 H Cl CH₃ CF₃ H NHCOOCH₃ 1-1360 H Cl CH₃ CF₃ HNHCOOC₂H₅ 1-1361 H Cl CH₃ CF₃ H NHCOO^(n)C₃H₇ 1-1362 H Cl CH₃ CF₃ HNHCOO^(i)C₃H₇ 1-1363 H Cl CH₃ CF₃ H NHCOO^(n)C₄H₉ 1-1364 H Cl CH₃ CF₃ HNHCOO^(n)C₅H₁₁ 1-1365 H Cl CH₃ CF₃ H NHCH₂COOCH₃ 1-1366 H Cl CH₃ CF₃ HNHCH₂COOC₂H₅ 1-1367 H Cl CH₃ CF₃ H NHCH₂COO^(n)C₃H₇ 1-1368 H Cl CH₃ CF₃H NHCH₂COO^(n)C₄H₉ 1-1369 H Cl CH₃ CF₃ H NHCH₂COO^(n)C₅H₁₁ 1-1370 H ClCH₃ CF₃ H NHCH₂COO^(i)C₃H₇ 1-1371 H Cl CH₃ CF₃ H NHCH₂COO^(c)C₅H₉ 1-1372H Cl CH₃ CF₃ H NHCH₂COO^(c)C₆H₁₁ 1-1373 F Cl CH₃ CF₃ HNHCH₂COO^(c)C_(6H) ₁₁ 1-1374 F Cl CH₃ CF₃ H NHCH(CH₃)COOCH₃ 1-1375 F ClCH₃ CF₃ H NHCH(CH₃)COOC₂H₅ 1-1376 F Cl CH₃ CF₃ H NHCH(CH₃)COO_(n)C₃H₇1-1377 F Cl CH₃ CF₃ H NHCH(CH₃)COO^(n)C₄H₉ 1-1378 F Cl CH₃ CF₃ HNHCH(CH₃)COO^(n)C₅H₁₁ 1-1379 F Cl CH₃ CF₃ H NHCH(CH₃)COO^(i)C₃H₇ 1-1380F Cl CH₃ CF₃ H NHCH(CH₃)COO^(c)C₅H₉ 1-1381 F Cl CH₃ CF₃ HNHCH(CH₃)COO^(c)C₆H₁₁ 1-1382 H Cl CH₃ CF₃ H OCH₃ 1-1383 H Cl CH₃ CF₃ HOC₂H₅ 1-1384 H Cl CH₃ CF₃ H O^(i)C₃H₇ 1-1385 H Cl CH₃ CF₃ H O^(n)C₃H₇1-1386 H Cl CH₃ CF₃ H OCH₂CH₂Cl 1-1387 H Cl CH₃ CF₃ H OCF₂CF₂H 1-1388 HCl CH₃ CF₃ H O^(c)C₅H₉ 1-1389 H Cl CH₃ CF₃ H O^(c)C₆H₁₁ 1-1390 H Cl CH₃CF₃ H OCH₂CH═CH₂ 1-1391 H Cl CH₃ CF₃ H OCH₂CCl═CH₂ 1-1392 H Cl CH₃ CF₃ HOCH₂CCl═COCl 1-1393 H Cl CH₃ CF₃ H OCH(CH₃)CH═CH₂ 1-1394 H Cl CH₃ CF₃ HOCH₂C≡CH 1-1395 H Cl CH₃ CF₃ H OCH(CH₃)C≡CH 1-1396 H Cl CH₃ CF₃ HOCH₂C≡CBr 1-1397 H Cl CH₃ CF₃ H OCH₂C≡CCl 1-1398 H Cl CH₃ CF₃ HOCH₂C≡CCH₂Cl 1-1399 H Cl CH₃ CF₃ H OCH₂CN 1-1400 H Cl CH₃ CF₃ H OCH₂OCH₃1-1401 H Cl CH₃ CF₃ H OCO₂OC₂H₅ 1-1402 H Cl CH₃ CF₃ H OCH₂SCH₃ 1-1403 HCl CH₃ CF₃ H OCH₂COOCH₃ 1-1404 H Cl CH₃ CF₃ H OCH₂COOC₂H₅ 1-1405 H ClCH₃ CF₃ H OCH₂COO^(n)C₃H₇ 1-1406 H Cl CH₃ CF₃ H OCH₂COO^(n)C₄H₉ 1-1407 HCl CH₃ CF₃ H OCH₂COO^(n)C₅H₁₁ 1-1408 H Cl CH₃ CF₃ H OCH₂COO^(i)C₃H₇1-1409 H Cl CH₃ CF₃ H OCH₂COO^(c)C₅H₉ 1-1410 H Cl CH₃ CF₃ HOCH₂COO^(c)C₆H₁₁ 1-1411 H Cl CH₃ CF₃ H OCH(CH₃)COOCH₃ 1-1412 H Cl CH₃CF₃ H OCH(CH₃)COOC₂H₅ 1-1413 H Cl CH₃ CF₃ H OCH(CH₃)COO^(n)C₃H₇ 1-1414 HCl CH₃ CF₃ H OCH(CH₃)COO^(n)C₄H₉ 1-1415 H Cl CH₃ CF₃ HOCH(CH₃)COO^(n)C₅H₁₁ 1-1416 H Cl CH₃ CF₃ H OCH(CH₃)COO^(i)C₃H₇ 1-1417 HCl CH₃ CF₃ H OCH(CH₃)COO^(c)C₅H₉ 1-1418 H Cl CH₃ CF₃ HOCH(CH₃)COO^(c)C₆H₁₁ 1-1419 H Cl CH₃ CF₃ H OCH₂CON(CH₃)₂ 1-1420 H Cl CH₃CF₃ H OCH₂CON(C₂H₅)₂ 1-1421 H Cl CH₃ CF₃ H OCH₂CON(CH₃)C₂H₅ 1-1422 H ClCH₃ CF₃ H OCH(CH₃)CON(CH₃)₂ 1-1423 H Cl CH₃ CF₃ H OCH(CH₃)CON(C₂H₅)1-1424 H Cl CH₃ CF₃ H OCH(CH₃)CON(CH₃)C₂H₅ 1-1425 H Cl CH₃ CF₃ HOCH₂COON(CH₃)₂ 1-1426 H Cl CH₃ CF₃ H OCH₂COON(C₂H₅)₂ 1-1427 H Cl CH₃ CF₃H OCH(CH₃)COON(CH₃)₂ 1-1428 H Cl CH₃ CF₃ H OCH(CH₃)COON(C₂H₅)₂ 1-1429 FCl CH₃ CF₃ H OCH₃ 1-1430 F Cl CH₃ CF₃ H OC₂H₅ 1-1431 F Cl CH₃ CF₃ HO^(i)C₃H₇ 1-1432 F Cl CH₃ CF₃ H O^(n)C₃H₇ 1-1433 F Cl CH₃ CF₃ HOCH₂CH₂Cl 1-1434 F Cl CH₃ CF₃ H OCF₂CF₂H 1-1435 F Cl CH₃ CF₃ H O^(c)C₅H₉1-1436 F Cl CH₃ CF₃ H O^(c)C₆H₁₁ 1-1437 F Cl CH₃ CF₃ H OCH₂CH═CH₂ 1-1438F Cl CH₃ CF₃ H OCH₂CCl=CH₂ 1-1439 F Cl CH₃ CF₃ H OCH₂CCl═CHCl 1-1440 FCl CH₃ CF₃ H OCH(CH₃)CH=CH₂ 1-1441 F Cl CH₃ CF₃ H OCH₂C≡CH 1-1442 F ClCH₃ CF₃ H OCH(CH₃)C≡CH 1-1443 F Cl CH₃ CF₃ H OCH₂C≡CBr 1-1444 F Cl CH₃CF₃ H OCH₂C≡CCl 1-1445 F Cl CH₃ CF₃ H OCH₂C≡CCH₂Cl 1-1446 F Cl CH₃ CF₃ HOCH₂CN 1-1447 F Cl CH₃ CF₃ H OCH₂OCH₃ 1-1448 F Cl CH₃ CF₃ H OCH₂OC₂H₅1-1449 F Cl CH₃ CF₃ H OCH₂SCH₃ 1-1450 F Cl CH₃ CF₃ H OCH₂COOCH₃ 1-1451 FCl CH₃ CF₃ H OCH₂COOC₂H₅ 1-1452 F Cl CH₃ CF₃ H OCH₂COO^(n)C₃H₇ 1-1453 FCl CH₃ CF₃ H OCH₂COO^(n)C₄H₉ 1-1454 F Cl CH₃ CF₃ H OCH₂COO^(n)C₅H₁₁1-1455 F Cl CH₃ CF₃ H OCH₂COO^(i)C₃H₇ 1-1456 F Cl CH₃ CF₃ HOCH₂COO^(c)C₅H₉ 1-1457 F Cl CH₃ CF₃ H OCH₂COO^(c)C₆H₁₁ 1-1458 F Cl CH₃CF₃ H OCH(CH₃)COOCH₃ 1-1459 F Cl CH₃ CF₃ H OCH(CH₃)COOC₂H₅ 1-1460 F ClCH₃ CF₃ H OCH(CH₃)COO^(n)C₃H₇ 1-1461 F Cl CH₃ CF₃ H OCH(CH₃)COO^(n)C₄H₉1-1462 F Cl CH₃ CF₃ H OCH(CH₃)COO^(n)C₅H₁₁ 1-1463 F Cl CH₃ CF₃ HOCH(CH₃)COO^(i)C₃H₇ 1-1464 F Cl CH₃ CF₃ H OCH(CH₃)COO^(c)C₅H₉ 1-1465 FCl CH₃ CF₃ H OCH(CH₃)COO^(c)C₆H₁₁ 1-1466 F Cl CH₃ CF₃ H OCH₂CON(CH₃)₂1-1467 F Cl CH₃ CF₃ H OCK CON(C₂H₅)₂ 1-1468 F Cl CH₃ CF₃ HOCH₂CON(CH₃)C₂H₆ 1-1469 F Cl CH₃ CF₃ H OCH(CH₃)CON(CH₃)₂ 1-1470 F Cl CH₃CF₃ H OCH(CH₃)CON(C₂H₅)₂ 1-1471 F Cl CH₃ CF₃ H OCH(CH₃)CON(CH₃)C₂H₅1-1472 F Cl CH₃ CF₃ H OCH₂COON(CH₃)₂ 1-1473 F Cl CH₃ CF₃ HOCH₂COON(C₂H₅)₂ 1-1474 F Cl CH₃ CF₃ H OCH(CH₃)COON(CH₃)₂ 1-1475 F Cl CH₃CF₃ H OCH(CH₃)COON(C₂H₅)₂ 1-1476 H F CH₃ CF H SH 1-1477 H Cl CH₃ CF₃ HSH 1-1478 H Br CH₃ CF₃ H SH 1-1479 F F CH₃ CF₃ H SH 1-1480 F Cl CH₃ CF₃H SH 1-1481 F Br CH₃ CF₃ H SH 1-1482 H Cl CH₃ CF₃ H SCH₃ 1-1483 H Cl CH₃CF₃ H SC₂H₅ 1-1484 H Cl CH₃ CF₃ H S^(i)C₃H₇ 1-1485 H Cl CH₃ CF₃ HSCH₂CH₂Cl 1-1486 H Cl CH₃ CF₃ H S^(c)C₅H₉ 1-1487 H Cl CH₃ CF₃ HS^(c)C₆H₁₁ 1-1488 H Cl CH₃ CF₃ H SCH₂CH═CH₂ 1-1489 H Cl CH₃ CF₃ HSCH₂CCl═CH₂ 1-1490 H Cl CH₃ CF₃ H SCH₂CCl═CHCl 1-1491 H Cl CH₃ CF₃ HSCH(CH₃)CH═CH₂ 1-1492 H Cl CH₃ CF₃ H SCH₂C≡CH 1-1493 H Cl CH₃ CF₃ HSCH(CH₃)C≡CH 1-1494 H Cl CH₃ CF₃ H SCH₂COOCH₃ 1-1495 H Cl CH₃ CF₃ HSCH₂COOC₂H₅ 1-1496 H Cl CH₃ CF₃ H SCH₂COO^(n)C₃H₇ 1-1497 H Cl CH₃ CF₃ HSCH₂COO^(n)C₄H₉ 1-1498 H Cl CH₃ CF₃ H SCH₂COO^(n)C₅H₁₁ 1-1499 H Cl CH₃CF₃ H SCH₂COO^(i)C₃H₇ 1-1500 H Cl CH₃ CF₃ H SCH₂COO^(c)C₅H₉ 1-1501 H ClCH₃ CF₃ H SCH₂COO^(c)C₆H₁₁ 1-1502 H Cl CH₃ CF₃ H SCH(CH₃)COOCH₃ 1-1503 HCl CH₃ CF₃ H SOH(CH₃)COOC₂H₅ 1-1504 H Cl CH₃ CF₃ H SCH(CH₃)COO^(n)C₃H₇1-1505 H Cl CH₃ CF₃ H SCH(CH₃)COO^(n)C₄H₉ 1-1506 H Cl CH₃ CF₃ HSCH(CH₃)COO^(n)C₅H₁₁ 1-1507 H Cl CH₃ CF₃ H SCH(CH₃)COO^(i)C₃H₇ 1-1508 HCl CH₃ CF₃ H SCH(CH₃)COO^(c)C₅H₉ 1-1509 H Cl CH₃ CF₃ H SCH(CH_(3)COO)^(c)C⁶H₁₁ 1-1510 H Cl CH₃ CF₃ H SCH₂CON(CH₃)₂ 1-1511 H Cl CH₃ CF₃ HSCH₂OON(C₂H₅)₂ 1-1512 H Cl CH₃ CF₃ H SCH₂CON(tetramethylene) 1-1513 H ClCH₃ CF₃ H SCH₂CON(pentalnethylene) 1-1514 H Cl CH₃ CF₃ H SCH₂CON(ethyleneoxyethylene) 1-1515 H Cl CH₃ CF₃ H SOH(CH₃)CON(CH₃)₂ 1-1516 HCl CH₃ CF₃ H SCH(CH₃)CON(C₂H₅)₂ 1-1517 H Cl CH₃ CF₃ H SCH(CH₃)CON(tetramethylene) 1-1518 H Cl CH₃ CF₃ H SCH(CH₃)CON (pentamethylene)1-1519 F Cl CH₃ CF₃ H SCH₃ 1-1520 F Cl CH₃ CF₃ H SC₂H₅ 1-1521 F Cl CH₃CF₃ H S^(i)C₃H₇ 1-1522 F Cl CH₃ CF₃ H SCH₂CH₂Cl 1-1523 F Cl CH₃ CF₃ HS^(c)C₅H₉ 1-1524 F Cl CH₃ CF₃ H S^(c)C₆H₁₁ 1-1525 F Cl CH₃ CF₃ HSCH₂CH═CH₂ 1-1526 F Cl CH₃ CF₃ H SCH₂CCl═CH₂ 1-1527 F Cl CH₃ CF₃ HSCH₂CCl═CHCl 1-1528 F Cl CH₃ CF₃ H SCH(CH₃)CH═CH₂ 1-1529 F Cl CH₃ CF₃ HSCH₂C≡CH 1-1530 F Cl CH₃ CF₃ H SCH(CH₃)C≡CH 1-1531 F Cl CH₃ CF₃ HSCH₂COOCH₃ 1-1532 F Cl CH₃ CF₃ H SCH₂COOC₂H₅ 1-1533 F Cl CH₃ CF₃ HSCH₂COO^(n)C₃H₇ 1-1534 F Cl CH₃ CF₃ H SCH₂COO^(n)C₄H₉ 1-1535 F Cl CH₃CF₃ H SCH₂COO^(n)C₅H₁₁ 1-1536 F Ci CH₃ CF₃ H SCH₂COO^(i)C₃H₇ 1-1537 F ClCH₃ CF₃ H SCH₂COO^(c)C₅H₉ 1-1538 F Cl CH₃ CF₃ H SCH₂COO^(c)C₆H₁₁ 1-1539F Cl CH₃ CF₃ H SCH(CH₃)COOCH₃ 1-1540 F Cl CH₃ CF₃ H SCH(CH₃)COOC₂H₅1-1541 F Cl CH₃ CF₃ H SCH(CH₃)COO^(n)C₃H₇ 1-1542 F Cl CH₃ CF₃ HSCH(CH₃)COO^(n)C₄H₉ 1-1543 F Cl CH₃ CF₃ H SCH(CH₃)COO^(n)C₅H₁₁ 1-1544 FCl CH₃ CF₃ H SCH(CH₃)COO^(i)C₃H₇ 1-1545 F Cl CH₃ CF₃ HSCH(CH₃)COO^(c)C₅H₉ 1-1546 F Cl CH₃ CF₃ H SCH(CH₃)COO^(c)C₆H₁₁ 1-1547 FCl CH₃ CF₃ H SCH₂CON(CH₃)₂ 1-1548 F Cl CH₃ CF₃ H SCH₂CON(C₂H₅)₂ 1-1549 FCl CH₃ CF₃ H SCH₂CON(tetramethylene) 1-1550 C F Cl CH₃ CF₃ HSCH₂CON(pentamethylene) 1-1551 F Cl CH₃ CF₃ H SCH₂CON(ethyleneoxyethylene) 1-1552 F Cl CH₃ CF₃ H SCH(CH₃)CON(CH₃)₂ 1-1553 FCl CH₃ CF₃ H SCH(CH₃)CON(C₂H)₂ 1-1554 F Cl CH₃ CF₃ H SCH(CH₃)CON(tetramethylene) 1-1555 F Cl CH_(3 CF) ₃ H SCH(CH₃)CON (pentamethylene)1-1556 H F CH₃ CF₃ H SO₂Cl 1-1557 H Cl CH₃ CF₃ H SO₂Cl 1-1558 H Br CH₃CF₃ H SO₂Cl 1-1559 F F CH₃ CF₃ H SO₂Cl 1-1560 F Cl CH₃ CF₃ H SO₂Cl1-1561 F Br CH₃ CF₃ H SO₂Cl 1-1562 H Cl CH₃ CF₃ H SO₂OCH₃ 1-1563 H ClCH₃ CF₃ H SO₂OC₂H₅ 1-1564 H Cl CH₃ CF₃ H SO₂O^(i)C₃H₇ 1-1565 H Cl CH₃CF₃ H SO₂OCH₂CH═CH₂ 1-1566 F Cl CH₃ CF₃ H SO₂OCH₃ 1-1567 F Cl CH₃ CF₃ HSO₂OC₂H₅ 1-1568 F Cl CH₃ CF₃ H SO₂O^(i)C₃H₇ 1-1569 F Cl CH₃ CF₃ HSO₂OCH₂CH═CH₂ 1-1570 H Cl CH₃ CF₃ H SO₂N(CH₃)₂ 1-1571 H Cl CH₃ CF₃ HSO₂N(C₂H₅)₂ 1-1572 F Cl CH₃ CF₃ H SO₂N(CH₃)₂ 1-1573 F Cl CH₃ CF₃ HSO₂N(C₂H₅)₂ 1-1574 H Cl CH₃ CF₃ H COOH 1-1575 H Cl CH₃ CF₃ H COOCH₃1-1576 H Cl CH₃ CF₃ H COOC₂H₅ 1-1577 H Cl CH₃ CF₃ H COO^(n)C₃H₇ 1-1578 HCl CH₃ CF₃ H COO^(n)C₄H₉ 1-1579 H Cl CH₃ CF₃ H COO^(n)C₅H₁₁ 1-1580 H ClCH₃ CF₃ H COO^(i)C₃H₇ 1-1581 H Cl CH₃ CF₃ H COOCH₂CH₂Cl 1-1582 H Cl CH₃CF₃ H COOCH₂CH₂Br 1-1583 H Cl CH₃ CF₃ H CON(CH₃)₂ 1-1584 H Cl CH₃ CF₃ HCONHCH₃ 1-1585 H Cl CH₃ CF₃ H CON(C₂H₅)₂ 1-1586 H Cl CH₃ CF₃ H CONHC₂H₅1-1587 H Cl CH₃ CF₃ H COCH₃ 1-1588 H Cl CH₃ CF₃ H COC₂H₅ 1-1589 H Cl CH₃CF₃ H COCH₂Cl 1-1590 H Cl CH₃ CF₃ H CHO 1-1591 H Cl CH₃ CF₃ HCH═CHCOOCH₃ 1-1592 H Cl CH₃ CF₃ H CH═CHCOOC₂H₅ 1-1593 H Cl CH₃ CF₃ HCH₂CH₂COOCH₃ 1-1594 H Cl CH₃ CF₃ H CH₂CH₂COOC₂H₅ 1-1595 F Cl CH₃ CF₃ HCOOH 1-1596 F Cl CH₃ CF₃ H COOCH₃ 1-1597 F Cl CH₃ CF₃ H COOC₂H₅ 1-1598 FCl CH₃ CF₃ H COO^(n)C₃H₇ 1-1599 F Cl CH₃ CF₃ H COO^(n)C₄H₉ 1-1600 F ClCH₃ CF₃ H COO^(n)C₅H₁₁ 1-1601 F Cl CH₃ CF₃ H COO^(i)C₃H₇ 1-1602 F Cl CH₃CF₃ H COOCH₂ CH₂Cl 1-1603 F Cl CH₃ CF₃ H COOCH₂ CH₂Br 1-1604 F Cl CH₃CF₃ H CON(CH₃)₂ 1-1605 F Cl CH₃ CF₃ H CONHCH₃ 1-1606 F Cl CH₃ CF₃ HCON(C₂H₅)₂ 1-1607 F Cl CH₃ CF₃ H CONHC₂H₅ 1-1608 F Cl CH₃ CF₃ H COCH₃1-1609 F Cl CH₃ CF₃ H COC₂H₅ 1-1610 F Cl CH₃ CF₃ H COCH₂Cl 1-1611 F ClCH₃ CF₃ H CHO 1-1612 F Cl CH₃ CF₃ H CH═CHCOOCH₃ 1-1613 F Cl CH₃ CF₃ HCH═CHCOOC₂H₅ 1-1614 F Cl CH₃ CF₃ H CH₂CH₂COOCH₃ 1-1615 F Cl CH₃ CF₃ HCH₂CO₂COOC₂H₅ 1-1616 H F CH₃ CF₃ H H 1-1617 H Cl CH₃ CF₃ H H 1-1618 H BrCH₃ CF₃ H H 1-1619 F F CH₃ CF₃ H H 1-1620 F Cl CH₃ CF₃ H H 1-1621 F BrCH₃ CF₃ H H 1-1622 F Cl H CF₃ CH₃ CH₂CHClCO₂C₂H₅ 1-1623 F Cl H CF₃ HCH₂CHClCO₂C₂H₅ 1-1624 F Cl H CF₃ CH₃ CH₂CHClCO₂CH₃ 1-1625 F Cl H CF₃ HCH₂CHClCO₂CH₃ 1-1626 F Cl H CF₃ H OCH₂CO₂H 1-1627 F Cl H CF₃ CH₃OCH₂CO₂H 1-1628 F Cl CH₃ CF₃ H OCH₂CO₂H 1-1629 F Cl H CF₃ H OCH(CH₃)CO₂H1-1630 F Cl H CF₃ CH₃ OCH(CH₃)CO₂H 1-1631 F Cl CH₃ CF₃ H OCH(CH₃)CO₂H1-1632 H Cl H CF₃ H OCH₂CO₂H 1-1633 H Cl H CF₃ CH₃ OCH₂CO₂H 1-1634 H ClCH₃ CF₃ H OCH₂CO₂H 1-1635 H Cl H CF₃ H OCH(CH₃)CO₂H 1-1636 H Cl H CF₃CH₃ OCH(CH₃)CO₂H 1-1637 H Cl CH₃ CF₃ H OCH(CH₃)CO₂H 1-1638 F Cl H CF₃ HSCH₂CO₂H 1-1639 F Cl H CF₃ CH₃ SCH₂CO₂H 1-1640 F Cl CH₃ CF₃ H SCH₂CO₂H1-1641 F Cl H CF₃ H SCH(CH₃)CO₂H 1-1642 F Cl H CF₃ CH₃ SCH(CH₃)CO₂H1-1643 F Cl CH₃ CF₃ H SCH(CH₃)CO₂H 1-1644 H Cl H CF₃ H SCH₂CO₂H 1-1645 HCl H CF CH₃ SCH₂CO₂H 1-1646 H Cl CH₃ CF₃ H SCH₂CO₂H 1-1647 H Cl H CF₃ HSCH(CH₃) CO₂H 1-1648 H Cl H CF₃ CH₃ SCH(CH₃)CO₂H 1-1649 H Cl CH₃ CF₃ HSCH(CH₃)CO₂H 1-1650 F Cl H CF₃ CH₃ OCH(C₂H₅)CO²CH₃ 1-1651 Cl Cl H CF₃ HOCH₂CO₂CH₃ 1-1652 Cl Cl H CF₃ H OCH₂CO₂C₂H₅ 1-1653 Cl Cl H CF₃ H OCH₂CO₂^(i)C₃H₇ 1-1654 Cl Cl H CF₃ CH₃ OCH₂CO₂CH₃ 1-1655 Cl Cl H CF₃ CH₃OCH₂CO₂C₂H₅ 1-1656 Cl Cl H CF₃ CH₃ OCH₂CO₂ ^(i)C₃H₇ 1-1657 Cl Cl CH₃ CF₃H OCH₂CO₂CH₃ 1-1658 Cl Cl CH₃ CF₃ H OCH₂CO₂C₂H₅ 1-1659 Cl Cl CH₃ CF₃ HOCH₂CO₂ ^(i)C₃H₇ 1-1660 Cl Cl H CF₃ H OCH₂C≡CH 1-1661 Cl Cl H CF₃ HOCH(CH₃)C≡CH 1-1662 Cl Cl H CF₃ H OCH(CH₃)CO₂C₂H₅ 1-1663 Cl Cl H CF₃ CH₃OCH₂C≡CH 1-1664 Cl Cl H CF₃ CH₃ OCH(CH₃)C≡CH 1-1665 Cl Cl H CF₃ CH₃OCH(CH₃)CO₂C₂H₅ 1-1666 Cl Cl CH₃ CF₃ H OCH₂C≡CH 1-1667 Cl Cl CH₃ CF₃ HOCH(CH₃)C≡CH 1-1668 Cl Cl CH₃ CF₃ H OClH(CH₃)CO₂C₂H₅ 1-1669 F Br H CF₃ HOCH₂CO₂CH₃ 1-1670 F Br H CF₂ H OCH₂CO₂C₂H₅ 1-1671 F Br H CF₃ H OCH₂CO₂^(i)C₃H₇ 1-1672 F Br H CF₃ CH₃ OCH₂CO₂CH₃ 1-1673 F Br H CF₃ CH₃OCH₂CO₂C₂H₅ 1-1674 F Br H CF₃ CH₃ OCH₂CO₂ ^(i)C₃H₇ 1-1675 F Br CH₃ CF₃ HOCH₂CO₂CH₃ 1-1676 F Br CH₃ CF₃ H OCH₂CO₂C₂H₅ 1-1677 F Br CH₃ CF₃ HOCH₂CO₂ ^(i)C₃H₇ 1-1678 F Br H CF₃ H OCH₂C≡CH 1-1679 F Br H CF₃ HOCH(CH₃)C≡CH 1-1680 F Br H CF₃ H OCH(CH₃)CO₂C₂H₅ 1-1681 F Br H CF₃ CH₃OCH₂C≡CH 1-1682 F Br H CF₃ CH₃ OCH(CH₃)C≡CH 1-1683 F Br H CF₃ CH₃OCH(CH₃)CO₂C₂H₅ 1-1684 F Br CH₃ CF₃ H OCH₂C≡CH 1-1685 F Br CH₃ CF₃ HOCH(CH₃)C≡CH 1-1686 F Br CH₃ CF₃ H OCH(CH₃)CO₂C₂H₅ 1-1687 Cl Cl H CF₃ HH 1-1688 Cl Cl H CF₃ H OH 1-1689 Cl Cl H CF₃ H NO₂ 1-1690 Cl Cl H CF₃ HNH₂ 1-1691 Cl Cl H CF₃ H NHSO₂CH₃ 1-1692 Cl Cl H CF₃ H NHSO₂CH₂Cl 1-1693Cl Cl H CF₃ H NHCH₂CO₂CH₃ 1-1694 Cl Cl H CF₃ H NHCH₂CO₂C₂H₅ 1-1695 Cl ClH CF₃ H NHCH₂CO₂ ^(i)C₃H₇ 1-1696 Cl Cl H CF₃ H NHCH(CH₃)CO₂CH₃ 1-1697 ClCl H CF₃ H NHCH(CH₃)CO₂C₂H₅ 1-1698 Cl Cl H CF₃ H NHCH(CH₃)CO₂ ^(i)C₃H₇1-1699 Cl Cl H CF₃ H CO₂H 1-1700 Cl Cl H CF₃ H CO₂CH₃ 1-1701 Cl Cl H CF₃H CO₂C₂H₅ 1-1702 Cl Cl H CF₃ H CO₂ ^(n)C₃H₇ 1-1703 Cl Cl H CF₃ H CO₂^(n)C₄H₉ 1-1704 Cl Cl H CF₃ H CO₂ ^(n)C₅H₁₁ 1-1705 Cl Cl H CF₃ H CO₂^(i)C₃H₇ 1-1706 Cl Cl H CF₃ H CO₂CH₂CH₂Cl 1-1707 Cl Cl H CF₃ HCO₂CH₂CH₂Br 1-1708 Cl Cl H CF₃ H CON(CH₃)₂ 1-1709 Cl Cl H CF₃ H CONHCH₃1-1710 Cl Cl H CF₃ H CON(C₂H₅)₂ 1-1711 Cl Cl H CF₃ H CONHC₂H₅ 1-1712 ClCl H CF₃ H COCH₃ 1-1713 Cl Cl H CF₃ H COC₂H₅ 1-1714 Cl Cl H CF₃ HCOCH₂Cl 1-1715 Cl Cl H CF₃ H CHO 1-1716 Cl Cl H CF₃ H CH═CHCO₂CH₃ 1-1717Cl Cl H CF₃ H O^(i)C₃H₇ 1-1718 Cl Cl H CF₃ CH₃ H 1-1719 Cl Cl H CF₃ CH₃OH 1-1720 Cl Cl H CF₃ CH₃ NO₂ 1-1721 Cl Cl H CF₃ CH₃ NH₂ 1-1722 Cl Cl HCF₃ CH₃ NHSO₂CH₃ 1-1723 Cl Cl H CF₃ CH₃ NHSO₂CH₂Cl 1-1724 Cl Cl H CF₃CH₃ NHCH₂CO₂CH₃ 1-1725 Cl Cl H CF₃ CH₃ NHCH₂CO₂C₂H₅ 1-1726 Cl Cl H CF₃CH₃ NHCH₂CO₂ ^(i)C₃H₇ 1-1727 Cl Cl H CF₃ CH₃ NHCH(CH₃)CO₂CH₃ 1-1728 ClCl H CF₃ CH₃ NHCH(CH₃)CO₂C₂H₅ 1-1729 Cl Cl H CF₃ CH₃ NHCH(CH₃)CO₂^(i)C₃H₇ 1-1730 Cl Cl H CF₃ CH₃ CO₂H 1-1731 Cl Cl H CF₃ CH₃ CO₂CH₃1-1732 Cl Cl H CF₃ CH₃ CO₂C₂H₅ 1-1733 Cl Cl H CF₃ CH₃ CO₂ ^(n)C₃H₇1-1734 Cl Cl H CF₃ CH₃ CO₂ ^(n)C₄H₉ 1-1735 Cl Cl H CF₃ CH₃ CO₂ ^(n)C₅H₁₁1-1736 Cl Cl H CF₃ CH₃ CO₂ ^(i)C₃H₇ 1-1737 Cl Cl H CF₃ CH₃ CO₂CH₂CH₂Cl1-1738 Cl Cl H CF₃ CH₃ CO₂CH₂CH₂Br 1-1739 Cl Cl H CF₃ CH₃ CON(CH₃)₂1-1740 Cl Cl H CF₃ CH₃ CONHCH₃ 1-1741 Cl Cl H CF₃ CH₃ CON(C₂H₅)₂ 1-1742Cl Cl H CF₃ CH₃ CONHC₂H₅ 1-1743 Cl Cl H CF₃ CH₃ COCH₃ 1-1744 Cl Cl H CF₃CH₃ COC₂H5 1-1745 Cl Cl H CF₃ CH₃ COCH₂Cl 1-1746 Cl Cl H CF₃ CH₃ CHO1-1747 Cl Cl H CF₃ CH₃ CH=CHCO₂CH₃ 1-1748 Cl Cl H CF₃ CH₃ O^(i)C₃H₇1-1749 Cl Cl CH₃ CF₃ H H 1-1750 Cl Cl CH₃ CF₃ H OH 1-1751 Cl Cl CH₃ CF₃H NO₂ 1-1752 Cl Cl CH₃ CF₃ H NH₂ 1-1753 Cl Cl CH₃ CF₃ H NHSO₂CH₃ 1-1754Cl Cl CH₃ CF₃ H NHSO₂CH₂Cl 1-1755 Cl Cl CH₃ CF₃ H NHCH₂CO₂CH₃ 1-1756 ClCl CH₃ CF₃ H NHCH₂CO₂C₂H₅ 1-1757 Cl Cl CH₃ CF₃ H NHCH₂CO₂ ^(i)C₃H₇1-1758 Cl Cl CH₃ CF₃ H NHCH(CH₃)CO₂CH₃ 1-1759 Cl Cl CH₃ CF₃ HNHCH(CH₃)CO₂C₂H₅ 1-1760 Cl Cl CH₃ CF₃ H NHCH(CH₃)CO₂ ^(i)C₃H₇ 1-1761 ClCl CH₃ CF₃ H CO₂H 1-1762 Cl Cl CH₃ CF₃ H CO₂CH₃ 1-1763 Cl Cl CH₃ CF₃ HCO₂C₂H₅ 1-1764 Cl Cl CH₃ CF₃ H CO₂ ^(n)C₃H₇ 1-1765 Cl Cl CH₃ CF₃ H CO₂^(n)C₄H₉ 1-1766 Cl Cl CH₃ CF₃ H CO₂ ^(n)C₅H₁₁ 1-1767 Cl Cl CH₃ CF₃ H CO₂^(i)C₃H₇ 1-1768 Cl Cl CH₃ CF₃ H CO₂CH₂CH₂Cl 1-1769 Cl Cl CH₃ CF₃ HCO₂CH₂CH₂Br 1-1770 Cl Cl CH₃ CF₃ H CON(CH₃)₂ 1-1771 Cl Cl CH₃ CF₃ HCONHCH₃ 1-1772 Cl Cl CH₃ CF₃ H CON(C₂H₅)₂ 1-1773 Cl Cl CH₃ CF₃ HCONHC₂H₅ 1-1774 Cl Cl CH₃ CF₃ H COCH₃ 1-1775 Cl Cl CH₃ CF₃ H COC₂H₅1-1776 Cl Cl CH₃ CF₃ H COCH₂Cl 1-1777 Cl Cl CH₃ CF₃ H CHO 1-1778 Cl ClCH₃ CF₃ H CH═CHCO₂CH₃ 1-1779 Cl Cl CH₃ CF₃ H O^(i)C₃H₇ 1-1780 F Br H CF₃H O^(i)C₃H₇ 1-1781 F Br H CF₃ H N(SO₂CH₃)₂ 1-1782 F Br H CF₃ H NHSO₂CH₃1-1783 F Br H CF₃ CH₃ O^(i)C₃H₇ 1-1784 F Br H CF₃ CH₃ N(SO₂CH₃)₂ 1-1785F Br H CF₃ CH₃ NHSO₂CH₃ 1-1786 F Br CH₃ CF₃ H O^(i)C₃H₇ 1-1787 F Br CH₃CF₃ H N(SO₂CH₃)₂ 1-1788 F Br CH₃ CF₃ H NHSO₂CH₃ 1-1789 F Cl H CF₃ CH₃OCH₂C(CH₃)=CH₂ 1-1790 F Cl H CF₃ CH₃ OCH₂CO₂C₇H₁₅ 1-1791 F Cl H CF₃ CH₃OCH₂CO₂C₈H₁₇ 1-1792 F Cl H CF₃ CH₃ COOCH₂C₆H₅ 1-1793 F Cl H CF₃ CH₃C(CH₃)NOH 1-1794 F Cl H CF₃ CH₃ C(CH₃)═NOCH₃ 1-1795 F Cl H CF₃ CH₃C(CH₃)═NOC₂H₅ 1-1796 F Cl H CF₃ CH₃ C(CH₃)═NO^(i)C₃H₇ 1-1797 F Cl H CF₃CH₃ C(C₂H₅)=NOH 1-1798 F Cl H CF₃ CH₃ C(C₂H₅)═NOCH₃ 1-1799 F Cl H CF₃CH₃ C(C₂H₅)═NOC₂H₅ 1-1800 F Cl H CF₃ CH₃ C(C₂H₅)═NO^(i)C₃H₇ 1-1801 F ClH CF₃ CH₃ C(CH₃)═NNH₂ 1-1802 F Cl H CF₃ CH₃ C(CH₃)=NNHCH₃ 1-1803 F Cl HCF₃ CH₃ C(CH₃)═NN(CH₃)₂ 1-1804 F Cl H CF₃ CH₃ C(CH₃)═NNHC₂H₅ 1-1805 F ClH CF₃ CH₃ C(CH₃)═NN(C₂H₅)₂ 1-1806 F Cl H CF₃ CH₃ C(C₂H₅)═NNH₂ 1-1807 FCl H CF₃ CH₃ C(C₂H₅)═NNHCH₃ 1-1808 F Cl H CF₃ CH₃ C(C₂H₅)═NN(CH₃)₂1-1809 F Cl H CF₃ CH₃ C(C₂H₅)═NNHC₂H₅ 1-1810 F Cl H CF₃ CH₃C(C₂H₅)═NN(C₂H₅)₂ 1-1811 F Cl H CF₃ CH₃ C(CH₃)(OCH₃)₂ 1-1812 F Cl H CF₃CH₃ C(CH₃)(OC₂H₅)₂ 1-1813 F Cl H CF₃ CH₃ C(CH₃)(C^(i)C₃H₇₎ ₂ 1-1814 F ClH CF₃ CH₃

1-1815 F Cl H CF₃ CH₃

1-1816 F Cl H CF₃ CH₃

1-1817 F Cl H CF₃ CH₃

1-1818 F Cl H CF₃ H OCH₂C(CH₃)═CH₂ 1-1819 F Cl H CF₃ H OCH₂CO₂C₇H₁₅1-1820 F Cl H CF₃ H OCH₂CO₂C₈H₁₇ 1-1821 F Cl H CF₃ H COOCH₂C₆H₅ 1-1822 FCl H CF₃ H C(CH₃)=NOH 1-1823 F Cl H CF₃ H C(CH₃)═NOCH₃ 1-1824 F Cl H CF₃H C(CH₃)═NOC₂H₅ 1-1825 F Cl H CF₃ H C(CH₃)=NO^(i)C₃H₇ 1-1826 F Cl H CF₃H C(C₂H₅)═NOH 1-1827 F Cl H CF₃ H C(C₂H₅)=NOCH₃ 1-1828 F Cl H CF₃ HC(C₂H₅)═NOC₂H₅ 1-1829 F Cl H CF₃ H C(C₂H₅)=NO^(i)C₃H₇ 1-1830 F Cl H CF₃H C(CH₃)=NNH₂ 1-1831 F Cl H CF₃ H C(CH₃)=NNHCH₃ 1-1832 F Cl H CF₃ HC(CH₃)=NN(CH₃)₂ 1-1833 F Cl H CF₃ H C(CH₃)═NNHC₂H₅ 1-1834 F Cl H CF₃ HC(CH₃)═NN(C₂H₅)₂ 1-1835 F Cl H CF₃ H C(C₂H₅)═NNH₂ 1-1836 F Cl H CF₃ HC(C₂H₅)═NNHCH₃ 1-1837 F Cl H CF₃ H C(C₂H₅)═NN(CH₃)₂ 1-1838 F Cl H CF₃ HC(C₂H₅)═NNHC₂H₅ 1-1839 F Cl H CF₃ H C(C₂H₅)═NN(C₂H₅)₂ 1-1840 F Cl H CF₃H C(CH₃)(OCH₃)₂ 1-1841 F Cl H CF₃ H C(CH₃)(OC₂H₅)₂ 1-1842 F Cl H CF₃ HC(CH₃)(C^(i)C₃H₇)₂ 1-1843 F Cl H CF₃ H

1-1844 F Cl H CF₃ H

1-1845 F Cl H CF₃ H

1-1846 F Cl H CF₃ H

1-1847 F Cl CH₃ CF₃ H OCH₂C(CH₃)CH₂ 1-1848 F Cl CH₃ CF₃ H OCH₂CO₂C₇H₁₅1-1849 F Cl CH₃ CF₃ H OCH₂CO₂C₈H₁₇ 1-1850 F Cl CH₃ CF₃ H COOCH₂C₆H₅1-1851 F Cl CH₃ CF₃ H C(CH₃)=NOH 1-1852 F Cl CH₃ CF₃ H C(CH₃)=NOCH₃1-1853 F Cl CH₃ CF₃ H C(CH₃)=NOC₂H₅ 1-1854 F Cl CH₃ CF₃ HC(CH₃)=NO^(i)C₃H₇ 1-1855 F Cl CH₃ CF₃ H C(C₂H₅)=NOH 1-1856 F Cl CH₃ CF₃H C(C₂H₅)=NOCH₃ 1-1857 F Cl CH₃ CF₃ H C(C₂H₅)=NOC₂H₅ 1-1858 F Cl CH₃ CF₃H C(C₂H₅)=NO^(i)C₃H₇ 1-1859 F Cl CH₃ CF₃ H C(CH₃)=NNH₂ 1-1860 F Cl CH₃CF₃ H C(CH₃)=NNCH₃ 1-1861 F Cl CH₃ CF₃ H C(CH₃)=NN(CH₃)₂ 1-1862 F Cl CH₃CF₃ H C(CH₃)=NNHC₂H₅ 1-1863 F Cl CH₃ CF₃ H C(CH₃)=NN(C₂H₅)₂ 1-1864 F ClCH₃ CF₃ H C(C₂H₅)═NNH₂ 1-1865 F Cl CH₃ CF₃ H C(C₂H₅)═NNHCH₃ 1-1866 F ClCH₃ CF₃ H C(C₂H₅)=NN(CH₃)₂ 1-1867 F Cl CH₃ CF₃ H C(C₂H₅)═NNHC₂H₅ 1-1868F Cl CH₃ CF₃ H C(C₂H₅)═NN(C₂H₅)₂ 1-1869 F Cl CH₃ CF₃ H C(CH₃)(OCH₃)₂1-1870 F Cl CH₃ CF₃ H C(CH₃)(OC₂H₅)₂ 1-1871 F Cl CH₃ CF₃ HC(CH₃)(C^(i)C₃H₇₎ ₂ 1-1872 F Cl CH₃ CF₃ H

1-1873 F Cl CH₃ CF₃ H

1-1874 F Cl CH₃ CF₃ H

1-1875 F Cl CH₃ CF₃ H

1-1876 H Cl H CF₃ CH₃ OCH₂C(CH₃)=CH₂ 1-1877 H Cl H CF₃ CH₃ OCH₂CO₂C₇H₁₅1-1878 H Cl H CF₂ CH₃ OCH₂CO₂C₈H₁₇ 1-1879 H Cl H CF₃ CH₃ COOCH₂C₆H₅1-1880 H Cl H CF₃ CH₃ C(CH₃)═NOH 1-1881 H Cl H CF₃ CH₃ C(CH₃)═NOCH₃1-1882 H Cl H CF₃ CH₃ C(CH₃)=NOC₂H₅ 1-1883 H Cl H CF₃ CH₃C(CH₃)═NO^(i)C₃H₇ 1-1884 H Cl H CF₃ CH₃ C(C₂H₅)=NOH 1-1885 H Cl H CF₃CH₃ C(C₂H₅)═NOCH₃ 1-1886 H Cl H CF₃ CH₃ C(C₂H₅)═NOC₂H₅ 1-1887 H Cl H CF₃CH₃ C(C₂H₅)═NO^(i)C₃H₇ 1-1888 H Cl H CF₃ CH₃ C(CH₃)═NNH₂ 1-1889 H Cl HCF₃ CH₃ C(CH₃)═NNHCH₃ 1-1890 H Cl H CF₃ CH₃ C(CH₃)═NN(CH₃)₂ 1-1891 H ClH CF₃ CH₃ C(CH₃)═NNHC₂H₅ 1-1892 H Cl H CF₃ CH₃ C(CH₃)═NN(C₂H₅)₂ 1-1893 HCl H CF₃ CH₃ C(C₂H₅)=NNH₂ 1-1894 H Cl H CF₃ CH₃ C(C₂H₅)=NNHCH₃ 1-1895 HCl H CF₃ CH₃ C(C₂H₅)=NN(CH₃)₂ 1-1896 H Cl H CF₃ CH₃ C(C₂H₅)═NNHC₂H₅1-1897 H Cl H CF₃ CH₃ C(C₂H₅)=NN(C₂H₅)₂ 1-1898 H Cl H CF₃ CH₃C(CH₃)(OCH₃)₂ 1-1899 H Cl H CF₃ CH₃ C(CH₃)(OC₂H₅)₂ 1-1900 H Cl H CF₃ CH₃C(CH₃)(C^(i)C₃H₇₎ ₂ 1-1901 H Cl H CF₃ CH₃

1-1902 H Cl H CF₃ CH₃

1-1903 H Cl H CF₃ CH₃

1-1904 H Cl H CF₃ CH₃

1-1905 H Cl H CF₃ H OCH₂C(CH₃)=CH₂ 1-1906 H Cl H CF₃ H OCH₂CO₂C₇H₁₅1-1907 H Cl H CF₃ H OCH₂CO₂C₈H₁₇ 1-1908 H Cl H CF₃ H COOCH₂C₆H₅ 1-1909 HCl H CF₃ H C(CH₃)═NOH 1-1910 H Cl H CF₃ H C(CH₃)═NOCH₃ 1-1911 H Cl H CF₃H C(CH₃)═NOC₂H₅ 1-1912 H Cl H CF₃ H C(CH₃)═NO^(i)C₃H₇ 1-1913 H Cl H CF₃H C(C₂H₅)=NOH 1-1914 H Cl H CF₃ H C(C₂H₅)═NOCH₃ 1-1915 H Cl H CF₃ HC(C₂H₅)═NOC₂H₅ 1-1916 H Cl H CF₃ H C(C₂H₅)═NO^(i)C₃H₇ 1-1917 H Cl H CF₃H C(CH₃)=NNH₂ 1-1918 H Cl H CF₃ H C(CH₃)═NNHCH₃ 1-1919 H Cl H CF₃ HC(CH₃)═NN(CH₃)₂ 1-1920 H Cl H CF₃ H C(CH₃)═NNHC₂H₅ 1-1921 H Cl H CF₃ HC(CH₃)═NN(C₂H₅)₂ 1-1922 H Cl H CF₃ H C(C₂H₅)═NNH₂ 1-1923 H Cl H CF₃ HC(C₂H₅)═NNHCH₃ 1-1924 H Cl H CF₃ H C(C₂H₅)=NN(CH₃)₂ 1-1925 H Cl H CF₃ HC(C₂H₅)=NNHC₂H₅ 1-1926 H Cl H CF₃ H C(C₂H₅)=NN(C₂H₅)₂ 1-1927 H Cl H CF₃H C(CH₃)(OCH₃)₂ 1-1928 H Cl H CF₃ H C(CH₃)(OC₂H₅)₂ 1-1929 H Cl H CF₃ HC(CH₃)(C^(i)C₃H₇₎ ₂ 1-1930 H Cl H CF₃ H

1-1931 H Cl H CF₃ H

1-1932 H Cl H CF₃ H

1-1933 H Cl H CF₃ H

1-1934 H Cl CH₃ CF₃ H OCH₂C(CH₃)=CH₂ 1-1935 H Cl CH₃ CF₃ H OCH₂CO₂C₇H₁₅1-1936 H Cl CH₃ CF₃ H OCH₂CO₂C₈H₁₇ 1-1937 H Cl CH₃ CF₃ H COOCH₂C₆H₅1-1938 H Cl CH₃ CF₃ H C(CH₃)=NOH 1-1939 H Cl CH₃ CF₃ H C(CH₃)=NOCH₃1-1940 H Cl CH₃ CF₃ H C(CH₃)=NOC₂H₅ 1-1941 H Cl CH₃ CF₃ HC(CH₃)=NO^(i)C₃H₇ 1-1942 H Cl CH₃ CF₃ H C(C₂H₅)=NOH 1-1943 H Cl CH₃ CF₃H C(C₂H₅)=NOCH₃ 1-1944 H Cl CH₃ CF₃ H C(C₂H₅)=NOC₂H₅ 1-1945 H Cl CH₃ CF₃H C(C₂H₅)=NO^(i)C₃H₇ 1-1946 H Cl CH₃ CF₃ H C(CH₃)=NNH₂ 1-1947 H Cl CH₃CF₃ H C(CH₃)=NNHCH₃ 1-1948 H Cl CH₃ CF₃ H C(CH₃)=NN(CH₃)₂ 1-1949 H ClCH₃ CF₃ H C(CH₃)=NNHC₂H₅ 1-1950 H Cl CH₃ CF₃ H C(CH₃)=NN(C₂H₅)₂ 1-1951 HCl CH₃ CF₃ H C(C₂H₅)=NNH₂ 1-1952 H Cl CH₃ CF₃ H C(C₂H₅)=NNHCH₃ 1-1953 HCl CH₃ CF₃ H C(C₂H₅)=NN(CH₃)₂ 1-1954 H Cl CH₃ CF₃ H C(C₂H₅)=NNHC₂H₅1-1955 H Cl CH₃ CF₃ H C(C₂H₅)=NN(C₂H₅)₂ 1-1956 H Cl CH₃ CF₃ HC(CH₃)(OCH₃)₂ 1-1957 H Cl CH₃ CF₃ H C(CH₃)(OC₂H₅)₂ 1-1958 H Cl CH₃ CF₃ HC(CH₃)(C^(i)C₃H₇₎ ₂ 1-1959 H Cl CH₃ CF₃ H

1-1960 H Cl CH₃ CF₃ H

1-1961 H Cl CH₃ CF₃ H

1-1962 H Cl CH₃ CF₃ H

1-1963 Cl Cl H CF₃ CH₃ OCH₂C(CH₃)═CH₂ 1-1964 Cl Cl H CF₃ CH₃OCH₂CO₂C₇H₁₅ 1-1965 Cl Cl H CF₃ CH₃ OCH₂CO₂C₈H₁₇ 1-1966 Cl Cl H CF₃ CH₃COOCH₂C₆H₅ 1-1967 Cl Cl H CF₃ CH₃ C(CH₃)═NOH 1-1968 Cl Cl H CF₃ CH₃C(CH₃)═NOCH₃ 1-1969 Cl Cl H CF₃ CH₃ C(CH₃)═NOC₂H₅ 1-1970 Cl Cl H CF₃ CH₃C(CH₃)═NO^(i)C₃H₇ 1-1971 Cl Cl H CF₃ CH₃ C(C₂H₅)═NOH 1-1972 Cl Cl H CF₃CH₃ C(C₂H₅)=NOCH₃ 1-1973 Cl Cl H CF₃ CH₃ C(C₂H₅)=NOC₂H5 1-1974 Cl Cl HCF₃ CH₃ C(C₂H₅)═NO^(i)C₃H₇ 1-1975 Cl Cl H CF₃ CH₃ C(CH₃)═NNH₂ 1-1976 ClCl H CF₃ CH₃ C(CH₃)=NNHCH₃ 1-1977 Cl Cl H CF₃ CH₃ C(CH₃)═NN(CH₃)₂ 1-1978Cl Cl H CF₃ CH₃ C(CH₃)═NNHC₂H₅ 1-1979 Cl Cl H CF₃ CH₃ C(CH₃)═NN(C₂H₅)₂1-1980 Cl Cl H CF₃ CH₃ C(C₂H₅)=NNH₂ 1-1981 Cl Cl H CF₃ CH₃C(C₂H₅)═NNHCH₃ 1-1982 Cl Cl H CF₃ CH₃ C(C₂H₅)═NN(CH₃)₂ 1-1983 Cl Cl HCF₃ CH₃ C(C₂H₅)═NNHC₂H₅ 1-1984 Cl Cl H CF₃ CH₃ C(C₂H₅)═NN(C₂H₅)₂ 1-1985Cl Cl H CF₃ CH₃ C(CH₃)(OCH₃)₂ 1-1986 Cl Cl H CF₃ CH₃ C(CH₃)(OC₂H₅)₂1-1987 Cl Cl H CF₃ CH₃ C(CH₃)(C1C₃H₇₎ ₂ 1-1988 Cl Cl H CF₃ CH₃

1-1989 Cl Cl H CF₃ CH₃

1-1990 Cl Cl H CF₃ CH₃

1-1991 Cl Cl H CF₃ CH₃

1-1992 Cl Cl H CF₃ H OCH₂C(CH₃)═CH₂ 1-1993 Cl Cl H CF₃ H OCH₂CO₂C₇H₁₅1-1994 Cl Cl H CF₃ H OCH₂CO₂C₈H₁₇ 1-1995 Cl Cl H CF₃ H COOCH₂C₆H₅ 1-1996Cl Cl H CF₃ H C(CH₃)═NOH 1-1997 Cl Cl H CF₃ H C(CH₃)═NOCH₃ 1-1998 Cl ClH CF₃ H C(CH₃)═NOC₂H₅ 1-1999 Cl Cl H CF₃ H C(CH₃)═NO^(i)C₃H₇ 1-2000 ClCl H CF₃ H C(C₂H₅)═NOH 1-2001 Cl Cl H CF₃ H C(C₂H₅)=NOCH₃ 1-2002 Cl Cl HCF₃ H C(C₂H₅)═NOC₂H₅ 1-2003 Cl Cl H CF₃ H C(C₂H₅)═NO^(i)C₃H₇ 1-2004 ClCl H CF₃ H C(CH₃)═NNH₂ 1-2005 Cl Cl H CF₃ H C(CH₃)=NNHCH₃ 1-2006 Cl Cl HCF₃ H C(CH₃)═NN(CH₃)₂ 1-2007 Cl Cl H CF₃ H C(CH₃)═NNHC₂H₅ 1-2008 Cl Cl HCF₃ H C(CH₃)═NN(C₂H₅)₂ 1-2009 Cl Cl H CF₃ H C(C₂H₅)=NNH₂ 1-2010 Cl Cl HCF₃ H C(C₂H₅)═NNHCH₃ 1-2011 Cl Cl H CF₃ H C(C₂H₅)=NN(CH₃)₂ 1-2012 Cl ClH CF₃ H C(C₂H₅)═NNHC₂H₅ 1-2013 Cl Cl H CF₃ H C(C₂H₅)=NN(C₂H₅)₂ 1-2014 ClCl H CF₃ H C(CH₃)(CCH₃)₂ 1-2015 Cl Cl H CF₃ H C(CH₃)(OC₂H₅)₂ 1-2016 ClCl H CF₃ H C(CH₃)(C^(i)C₃H₇₎ ₂ 1-2017 Cl Cl H CF₃ H

1-2018 Cl Cl H CF₃ H

1-2019 Cl Cl H CF₃ H

1-2020 Cl Cl H CF₃ H

1-2021 Cl Cl CH₃ CF₃ H OCH₂C(CH₃)CH₂ 1-2022 Cl Cl CH₃ CF₃ H OCH₂CO₂C₇H₁₅1-2023 Cl Cl CH₃ CF₃ H OCH₂CO₂C₈H₁₇ 1-2024 Cl Cl CH₃ CF₃ H COOCH₂C₆H₅1-2025 Cl Cl CH₃ CF₃ H C(CH₃)=NOH 1-2026 Cl Cl CH₃ CF₃ H C(CH₃)=NOCH₃1-2027 Cl Cl CH₃ CF₃ H C(CH₃)=NOC₂H₅ 1-2028 Cl Cl CH₃ CF₃ HC(CH₃)=NO^(i)C₃H₇ 1-2029 Cl Cl CH₃ CF₃ H C(C₂H₅)═NOH 1-2030 Cl Cl CH₃CF₃ H C(C₂H₅)═NOCH₃ 1-2031 Cl Cl CH₃ CF₃ H C(C₂H₅)=NOC₂H₅ 1-2032 Cl ClCH₃ CF₃ H C(C₂H₅)═NO^(i)C₃H₇ 1-2033 Cl Cl CH₃ CF₃ H C(CH₃)═NNH₂ 1-2034Cl Cl CH₃ CF₃ H C(CH₃)=NNHCH₃ 1-2035 Cl Cl CH₃ CF₃ H C(CH₃)═NN(CH₃)₂1-2036 Cl Cl CH₃ CF₃ H C(CH₃)=NNHC₂H₅ 1-2037 Cl Cl CH₃ CF₃ HC(CH₃)═NN(C₂H₅)₂ 1-2038 Cl Cl CH₃ CF₃ H C(C₂H₅)═NNH₂ 1-2039 Cl Cl CH₃CF₃ H C(C₂H₅)═NNHCH₃ 1-2040 Cl Cl CH₃ CF₃ H C(C₂H₅)=NN(CH₃)₂ 1-2041 ClCl CH₃ CF₃ H C(C₂H₅)═NNHC₂H₅ 1-2042 Cl Cl CH₃ CF₃ H C(C₂H₅)═NN(C₂H₅)₂1-2043 Cl Cl CH₃ CF₃ H C(CH₃)(OCH₃)₂ 1-2044 Cl Cl CH₃ CF₃ HC(CH₃)(OC₂H₅)₂ 1-2045 Cl Cl CH₃ CF₃ H C(CH₃)(C^(i)C₃H₇₎ ₂ 1-2046 Cl ClCH₃ CF₃ H

1-2047 Cl Cl CH₃ CF₃ H

1-2048 Cl Cl CH₃ CF₃ H

1-2049 Cl Cl CH₃ CF₃ H

1-2050 F Cl H CF₃ CH₃ OCH₂COOCH₂COOCH₃ 1-2051 F Cl H CF₃ CH₃OCH₂COOCH₂COOC₂H₅ 1-2052 F Cl H CF₃ CH₃ OCH₂COOCH₂COO^(i)C₃H₇ 1-2053 FCl H CF₃ CH₃ OCH₂COOCH(CH₃)COOCH₃ 1-2054 F Cl H CF₃ CH₃OCH₂COOCH(CH₃)COOC₂H₅ 1-2055 F Cl H CF₃ CH₃ OCH₂COOCH(CH₃)COO^(i)C₃H₇1-2056 F Cl H CF₃ CH₃ OCH(CH₃)COOCH₂COOCH₃ 1-2057 F Cl H CF₃ CH₃OCH(CH₃)COOCH₂COOC₂HS 1-2058 F Cl H CF₃ CH₃ OCH(CH₃)COOCH₂COO^(i)C₃H₇1-2059 F Cl H CF₃ CH₃ OCH(CH₃)COOCH(CH₃)COOCH₃ 1-2060 F Cl H CF₃ CH₃OCH(CH₃)COOCH(CH₃)COOC₂H₅ 1-2061 F Cl H CF₃ CH₃OCH(CH₃)COOCH(CH₃)COO^(i)C₃H₇ 1-2062 F Cl H CF₃ H OCH₂COOCH₂COOCH₃1-2063 F Cl H CF₃ H OCH₂COOCH₂COOC₂H₅ 1-2064 F Cl H CF₃ HOCH₂COOCH₂COO^(i)C₃H₇ 1-2065 F Cl H CF₃ H OCH₂COOCH(CH₃)COOCH₃ 1-2066 FCl H CF₃ H OCH₂COOCH(CH₃)COOC₂H₅ 1-2067 F Cl H CF₃ HOCH₂COOCH(CH₃)COO^(i)C₃H₇ 1-2068 F Cl H CF₃ H OCH(CH₃)COOCH₂COOCH₃1-2069 F Cl H CF₃ H OCH(CH₃)COOCH₂COOC₂H₅ 1-2070 F Cl H CF₃ HOCH(CH₃)COOCH₂COO^(i)C₃H₇ 1-2071 F Cl H CF₃ H OCH(CH₃)COOCH(CH₃)COOCH₃1-2072 F Cl H CF₃ H OCH(CH₃)COOCH(CH₃)COOC₂H₅ 1-2073 F Cl H CF₃ HOCH(CH₃)COOCH(CH₃)COO^(i)C₃H₇ 1-2074 F Cl CH₃ CF₃ H OCH₂COOCH₂COOCH₃1-2075 F Cl CH₃ CF₃ H OCH₂COOCH₂COOC₂H₅ 1-2076 F Cl CH₃ CF₃ HOCH₂COOCH₂COO^(i)C₃H₇ 1-2077 F Cl CH₃ CF₃ H OCH₂COOCH(CH₃)COOCH₃ 1-2078F Cl CH₃ CF₃ H OCH₂COOCH(CH₃)COOC₂H₅ 1-2079 F Cl CH₃ CF₃ HOCH₂COOCH(CH₃)COO^(i)C₃H₇ 1-2080 F Cl CH₃ CF₃ H OCH(CH₃)COOCH₂COOCH₃1-2081 F Cl CH₃ CF₃ H OCH(CH₃)COOCH₂COOC₂H₅ 1-2082 F Cl CH₃ CF₃ HOCH(CH₃)COOCH₂COO^(i)C₃H₇ 1-2083 F Cl CH₃ CF₃ H OCH(CH₃)COOCH(CH₃)COOCH₃1-2084 F Cl CH₃ CF₃ H OCH(CH₃)COOCH(CH₃)COOC₂H₅ 1-2085 F Cl CH₃ CF₃ HOCH(CH₃)COOCH(CH₃)COO^(i)C₃H₇ 1-2086 H Cl H CF₃ CH₃ OCH₂COOCH₂COOCH₃1-2087 H Cl H CF₃ CH₃ OCH₂COOCH₂COOC₂H₅ 1-2088 H Cl H CF₃ CH₃OCH₂COOCH₂COO^(i)C₃H₇ 1-2089 H Cl H CF₃ CH₃ OCH₂COOCH(CH₃)COOCH₃ 1-2090H Cl H CF₃ CH₃ OCH₂COOCH(CH₃)COOC₂H₅ 1-2091 H Cl H CF₃ CH₃OCH₂COOCH(CH₃)COO^(i)C₃H₇ 1-2092 H Cl H CF₃ CH₃ OCH(CH₃)COOCH₂COOCH₃1-2093 H Cl H CF₃ CH₃ OCH(CH₃)COOCH₂COOC₂H₅ 1-2094 H Cl H CF₃ CH₃OCH(CH₃)COOCH₂COO^(i)C₃H₇ 1-2095 H Cl H CF₃ CH₃ OCH(CH₃)COOCH(CH₃)COOCH₃1-2096 H Cl H CF₃ CH₃ OCH(CH₃)COOCH(CH₃)COOC₂H₅ 1-2097 H Cl H CF₃ CH₃OCH(CH₃)COOCH(CH₃)CO01C₃H₇ 1-2098 H Cl H CF₃ H OCH₂COOCH₂COOCH₃ 1-2099 HCl H CF₃ H OCH₂COOCH₂COOC₂H₅ 1-2100 H Cl H CF₃ H OCH₂COOCH₂COO^(i)C₃H₇1-2101 H Cl H CF₃ H OCH₂COOCH(CH₃)COOCH₃ 1-2102 H Cl H CF₃ HOCH₂COOCH(CH₃)COOC₂H₅ 1-2103 H Cl H CF₃ H OCH₂COOCH(CH₃)COO^(i)C₃H₇1-2104 H Cl H CF₃ H OCH(CH₃)COOCH₂COOCH₃ 1-2105 H Cl H CF₃ HOCH(CH₃)COOCH₂COOC₂H₅ 1-2106 H Cl H CF₃ H OCH(CH₃)COOCH₂COO^(i)C₃H₇1-2107 H Cl H CF₃ H OCH(CH₃)COOCH(CH₃)COOCH₃ 1-2108 H Cl H CF₃ HOCH(CH₃)COOCH(CH₃)COOC₂H₅ 1-2109 H Cl H CF₃ HOCH(CH₃)COOCH(CH₃)COO^(i)C₃H₇ 1-2110 H Cl CH₃ CF₃ H OCH₂COOCH₂COOCH₃1-2111 H Cl CH₃ CF₃ H OCH₂COOCH₂COOC₂H₅ 1-2112 H Cl CH₃ CF₃ HOCH₂COOCH₂COO^(i)C₃H₇ 1-2113 H Cl CH₃ CF₃ H OCH₂COOCH(CH₃)COOCH₃ 1-2114H Cl CH₃ CF₃ H OCH₂COOCH(CH₃)COOC₂H₅ 1-2115 H Cl CH₃ CF₃ HOCH₂COOCH(CH₃)COO^(i)C₃H₇ 1-2116 H Cl CH₃ CF₃ H OCH(CH₃)COOCH₂COOCH₃1-2117 H Cl CH₃ CF₃ H OCH(CH₃)COOCH₂COOC₂H₅ 1-2118 H Cl CH₃ CF₃ HOCH(CH₃)COOCH₂COO^(i)C₃H₇ 1-2119 H Cl CH₃ CF₃ H OCH(CH₃)COOCH(CH₃)COOCH₃1-2120 H Cl CH₃ CF₃ H OCH(CH₃)COOCH(CH₃)COOC₂H₅ 1-2121 H Cl CH₃ CF₃ HOCH(CH₃)COOCH(CH₃)COO^(i)C₃H₇ 1-2122 Cl Cl H CF₃ CH₃ OCH₂COOCH₂COOCH₃1-2123 Cl Cl H CF₃ CH₃ OCH₂COOCH₂COOC₂H₅ 1-2124 Cl Cl H CF₃ CH₃OCH₂COOCH₂COO^(i)C₃H₇ 1-2125 Cl Cl H CF₃ CH₃ OCH₂COOCH(CH₃)COOCH₃ 1-2126Cl Cl H CF₃ CH₃ OCH₂COOCH(CH₃)COOC₂H₅ 1-2127 Cl Cl H CF₃ CH₃OCH₂COOCH(CH₃)COO^(i)C₃H₇ 1-2128 Cl Cl H CF₃ CH₃ OCH(CH₃)COOCH₂COOCH₃1-2129 Cl Cl H CF₃ CH₃ OCH(CH₃)COOCH₂COOC₂H₅ 1-2130 Cl Cl H CF₃ CH₃OCH(CH₃)COOCH₂COO^(i)C₃H₇ 1-2131 Cl Cl H CF₃ CH₃OCH(CH₃)COOCH(CH₃)COOCH₃ 1-2132 Cl Cl H CF₃ CH₃OCH(CH₃)COOCH(CH₃)COOC₂H₅ 1-2133 Cl Cl H CF₃ CH₃OCH(CH₃)COOCH(CH₃)COO^(i)C₃H₇ 1-2134 Cl Cl H CF₃ H OCH₂COOCH₂COOCH₃1-2135 Cl Cl H CF₃ H OCH₂COOCH₂COOC₂H₅ 1-2136 Cl Cl H CF₃ HOCH₂COOCH₂COO^(i)C₃H₇ 1-2137 Cl Cl H CF₃ H OCH₂COOCH(CH₃)COOCH₃ 1-2138Cl Cl H CF₃ H OCH₂COOCH(CH₃)COOC₂H₅ 1-2139 Cl Cl H CF₃ HOCH₂COOCH(CH₃)COO^(i)C₃H₇ 1-2140 Cl Cl H CF₃ H OCH(CH₃)COOCH₂COOCH₃1-2141 Cl Cl H CF₃ H OCH(CH₃)COOCH₂COOC₂H₅ 1-2142 Cl Cl H CF₃ HOCH(CH₃)COOCH₂COO^(i)C₃H₇ 1-2143 Cl Cl H CF₃ H OCH(CH₃)COOCH(CH₃)COOCH₃1-2144 Cl Cl H CF₃ H OCH(CH₃)COOCH(CH₃)COOC₂H₅ 1-2145 Cl Cl H CF₃ HOCH(CH₃)COOCH(CH₃)COO^(i)C₃H₇ 1-2146 Cl Cl CH₃ CF₃ H OCH₂COOCH₂COOCH₃1-2147 Cl Cl CH₃ CF₃ H OCH₂COOCH₂COOC₂H₅ 1-2148 Cl Cl CH₃ CF₃ HOCH₂COOCH₂COO^(i)C₃H₇ 1-2149 Cl Cl CH₃ CF₃ H OCH₂COOCH(CH₃)COOCH₃ 1-2150Cl Cl CH₃ CF₃ H OCH₂COOCH(CH₃)COOC₂H₅ 1-2151 Cl Cl CH₃ CF₃ HOCH₂COOCH(CH₃)COO^(i)C₃H₇ 1-2152 Cl Cl CH₃ CF₃ H OCH(CH₃)COOCH₂COOCH₃1-2153 Cl Cl CH₃ CF₃ H OCH(CH₃)COOCH₂COOC₂H₅ 1-2154 Cl Cl CH₃ CF₃ HOCH(CH₃)COOCH₂COO^(i)C₃H₇ 1-2155 Cl Cl CH₃ CF₃ HOCH(CH₃)COOCH(CH₃)COOCH₃ 1-2156 Cl Cl CH₃ CF₃ HOCH(CH₃)COOCH(CH₃)COOC₂H₅ 1-2157 Cl Cl CH₃ CF₃ HOCH(CH₃)COOCH(CH₃)COO^(i)C₃H₇

[0805] TABLE 2 Compounds of the formula:

Compound No. X Z¹ n R³ R¹ R² R⁴ R⁵ 2-1 H O 1 H CF₂Cl CH₃ H H 2-2 H O 1 HCF₂Cl CH₃ H CH₃ 2-3 H O 1 H CF₂Cl CH₃ H C₂H₅ 2-4 H O 1 H CF₂Cl CH₃ H^(n)C₃H₇ 2-5 H O 1 H CF₂Cl CH₃ H ^(l)C₃H₇ 2-6 H O 1 H CF₂Cl CH₃ H^(l)C₄H₉ 2-7 H O 1 H CF₂Cl CH₃ H ^(n)C₄H₉ 2-8 H O 1 H CF₂Cl CH₃ HCH₂CH₂Cl 2-9 H O 1 H CF₂Cl CH₃ H CH₂CH₂Br 2-10 H O 1 H CF₂Cl CH₃ HCH₂CH═CH₂ 2-11 H O 1 H CF₂Cl CH₃ H CH(CH₃)CH═CH₂ 2-12 H O 1 H CF₂Cl CH₃H CH₂CCl═CH₂ 2-13 H O 1 H CF₂Cl CH₃ H CH₂C≡CH 2-14 H O 1 H CF₂Cl CH₃ HCH(CH₂)C≡CH 2-15 H O 1 H CF₂ Cl CH₃ H CH₂CN 2-16 H O 1 H CF₂ Cl CH₃ HCH₂OCH₃ 2-17 H O 1 H CF₂ Cl CH₃ H CH₂OC₂H₅ 2-18 H O 1 H CF₂ Cl CH₃ HCH₂COOH 2-19 H O 1 H CF₂ Cl CH₃ H CH₂COOCH₃ 2-20 H O 1 H CF₂ Cl CH₃ HCH₂COOC₂H₅ 2-21 H O 1 H CF₂ Cl CH₃ H CH₂COO^(n)C₃H₇ 2-22 H O 1 H CF₂ ClCH₃ H CH₂COO^(n−)C₄H₉ 2-23 H O 1 H CF₂ Cl CH₃ H CH₂COO^(n)C₅H₁₁ 2-24 H O1 H CF₂ Cl CH₃ H CH₂COO^(l)C₃H₇ 2-25 H O 1 H CF₂ Cl CH₃ H CH₂COO^(c)C₅H₉2-26 H O 1 H CF₂ Cl CH₃ H CH₂COO^(c)C₆H₁₁ 2-27 H O 1 H CF₂ Cl CH₃ HCH(CH₃)COOH 2-28 H O 1 H CF₂ Cl CH₃ H CH(CH₃)COOCH₃ 2-29 H O 1 H CF₂ ClCH₃ H CH(CH₃)COOC₂H₅ 2-30 H O 1 H CF₂ Cl CH₃ H CH(CH₃)COO^(n)C₃H₇ 2-31 HO 1 H CF₂ Cl CH₃ H CH(CH₃)COO^(n)C₄H₉ 2-32 H O 1 H CF₂ Cl CH₃ HCH(CH₃)COO^(n)C₅H₁₁ 2-33 H O 1 H CF₂ Cl CH₃ H CH(CH₃)COO^(l)C₃H₇ 2-34 HO 1 H CF₂ Cl CH₃ H CH(CH₃)COO^(c)C₅H₉ 2-35 H O 1 H CF₂ Cl CH₃ HCH(CH₃)COO^(c)C₆H₁₁ 2-36 H O 1 H CF₂ Cl CH₃ CH₃ H 2-37 H O 1 H CF₂ ClCH₃ CH₃ CH₃ 2-38 H O 1 H CF₂Cl CH₃ CH₃ C₂H₅ 2-39 H O 1 H CF₂Cl CH₃ CH₃^(n)C₃H₇ 2-40 H O 1 H CF₂Cl CH₃ CH₃ ^(l)C₃H₇ 2-41 H O 1 H CF₂Cl CH₃ CH₃^(l)C₄H₉ 2-42 H O 1 H CF₂Cl CH₃ CH₃ ^(n)C₄H₉ 2-43 H O 1 H CF₂Cl CH₃ CH₃CH₂CH═CH₂ 2-44 H O 1 H CF₂Cl CH₃ CH₃ CH(CH₃)CH═CH₂ 2-45 H O 1 H CF₂ClCH₃ CH₃ CH₂C≡CH 2-46 H O I H CF₂Cl CH₃ CH₃ CH(CH₃)C≡CH 2-47 H O 1 HCF₂Cl CH₃ CH₃ CH₂OCH₃ 2-48 H O 1 H CF₂Cl CH₃ CH₃ CH₂OC₂H₅ 2-49 F O 1 HCF₂Cl CH₃ H H 2-50 F O 1 H CF₂Cl CH₃ H CH₃ 2-51 F O 1 H CF₂Cl CH₃ H C₂H₅2-52 F O 1 H CF₂Cl CH₃ H ^(n)C₃H₇ 2-53 F O 1 H CF₂Cl CH₃ H ^(l)C₃H₇ 2-54F O 1 H CF₂Cl CH₃ H ^(l)C₄H₇ 2-55 F O 1 H CF₂Cl CH₃ H ^(n)C₄H₉ 2-56 F O1 H CF₂Cl CH₃ H CH₂CH₂Cl 2-57 F O 1 H CF₂Cl CH₃ H CH₂CH₂Br 2-58 F O 1 HCF₂Cl CH₃ H CH₂CH═CH₂ 2-59 F O 1 H CF₂Cl CH₃ H CH(CH₃)CH═CH₂ 2-60 F O 1H CF₂Cl CH₃ H CH₂CCl═CH₂ 2-61 F O 1 H CF₂Cl CH₃ H CH₂C≡CH 2-62 F O 1 HCF₂Cl CH₃ H CH(CH₃)C≡CH 2-63 F O 1 H CF₂Cl CH₃ H CH₂CN 2-64 F O 1 HCF₂Cl CH₃ H CH₂OCH₃ 2-65 F O 1 H CF₂Cl CH₃ H CH₂OC₂H₅ 2-66 F O 1 H CF₂ClCH₃ H CH₂COOH 2-67 F O 1 H CF₂Cl CH₃ H CH₂COOCH₃ 2-68 F O 1 H CF₂Cl CH₃H CH₂COOC₂ ⁻H₅ 2-69 F O 1 H CF₂Cl CH₃ H CH₂COO^(n)C₃H₇ 2-70 F O 1 HCF₂Cl CH₃ H CH₂COO^(n)C₄H₉ 2-71 F O 1 H CF₂Cl CH₃ H CH₂COO^(n)C₅H₁₁ 2-72F O 1 H CF₂Cl CH₃ H CH₂COO^(l)C₃H₇ 2-73 F O 1 H CF₂Cl CH₃ HCH₂COO^(c)C₅H₉ 2-74 F O 1 H CF₂Cl CH₃ H CH₂COO^(c)C₆H₁₁ 2-75 F 0 1 HCF₂Cl CH₃ H CH(CH₃)COOH 2-76 F O 1 H CF₂Cl CH₃ H CH(CH₃)COOCH₃ 2-77 F O1 H CF₂Cl CH₃ H CH(CH₃)COOC₂H₅ 2-78 F O 1 H CF₂Cl CH₃ HCH(CH₃)COO^(n)C₃H₇ 2-79 F O 1 H CF₂Cl CH₃ H CH(CH₃)COO^(n)C₄H₉ 2-80 F O1 H CF₂Cl CH₃ H CH(CH₃)COO^(n)C₅H₅ 2-81 F O 1 H CF₂Cl CH₃ HCH(CH₃)COO^(i)C₃H₇ 2-82 F O 1 H CF₂Cl CH₃ H CH(CH₃)COO^(c)C₅H₉ 2-83 F O1 H CF₂Cl CH₃ H CH(CH₃)COO^(c)C₆H₁₁ 2-84 F O 1 H CF₂Cl CH₃ CH₃ H 2-85 FO 1 H CF₂Cl CH₃ CH₃ CH₃ 2-86 F O 1 H CF₂Cl CH₃ CH₃ C₂H₆ 2-87 F O 1 HCF₂Cl CH₃ CH₃ ^(n)C₃H₇ 2-88 F O 1 H CF₂Cl CH₃ CH₃ ^(i)C₃H₇ 2-89 F O 1 HCF₂Cl CH₃ CH₃ ^(i)C₄H₉ 2-90 F O 1 H CF₂Cl CH₃ CH₃ ^(n)C₄H₉ 2-91 F O 1 HCF₂Cl CH₃ CH₃ CH₂CH═^(—CH) ₂ 2-92 F O 1 H CF₂Cl CH₃ CH₃ CH(CH₃)CH═CH₂2-93 F O 1 H CF₂Cl CH₃ CH₃ CH₂C≡CH 2-94 F O 1 H CF₂Cl CH₃ CH₃CH(CH₃)C≡CH 2-95 F O 1 H CF₂Cl CH₃ CH₃ CH₂OCH₃ 2-96 F O 1 H CF₂Cl CH₃CH₃ CH₂OC₂H₅ 2-97 H S 0 H CF₂Cl CH₃ — H 2-98 H S 0 H CF₂Cl CH₃ — CH₃2-99 H S 0 H CF₂Cl CH₃ — C₂H₅ 2-100 H S 0 H CF₂Cl CH₃ — ^(n)C₃H₇ 2-101 HS 0 H CF₂Cl CH₃ — ^(n)C₄H₉ 2-102 H S 0 H CF₂Cl CH₃ — ^(i)C₃H₇ 2-103 H S0 H CF₂Cl CH₃ — ^(i)C₄H₉ 2-104 H S 0 H CF₂Cl CH₃ — CH₂CH₂Cl 2-105 H S 0H CF₂Cl CH₃ — CH₂CH₂Br 2-106 H S 0 H CF₂Cl CH₃ — CH₂CH═CH₂ 2-107 H S 0 HCF₂Cl CH₃ — CH(CH₃)CH═CH₂ 2-108 H S 0 H CF₂Cl CH₃ — CH₂CCl ═CH₂ 2-109 HS 0 H CF₂Cl CH₃ — CH₂C≡CH 2-110 H S 0 H CF₂Cl CH₃ — CH(CH₃)C≡CH 2-111 HS 0 H CF₂Cl CH₃ — CH₂CN 2-112 H S 0 H CF₂Cl CH₃ — CH₂OCH₃ 2-113 H S 0 HCF₂Cl CH₃ — CH₂OC₂ ^(−H) ₅ 2-114 H S 0 H CF₂Cl CH₃ — CH₂COOH 2-115 H S 0H CF₂Cl CH₃ — CH₂COOCH₃ 2-116 H S 0 H CF₂ Cl CH₃ — CH₂COOC₂H₅ 2-117 H S0 H CF₂ Cl CH₃ — CH₂COO^(n)C₃H₇ 2-118 H S 0 H CF₂ Cl CH₃ —CH₂COO^(n)C₄H₉ 2-119 H S 0 H CF₂ Cl CH₃ — CH₂COO^(n)C₅H₁₁ 2-120 H S 0 HCF₂ Cl CH₃ — CH₂COO^(i)C₃H₇ 2-121 H S 0 H CF₂ Cl CH₃ — CH₂COO^(c)C₅H₉2-122 H S 0 H CF₂ Cl CH₃ — CH₂COO^(c)C₆H₁₁ 2-123 H S 0 H CF₂ Cl CH₃ —CH(CH₃)COOH 2-124 H S 0 H CF₂ Cl CH₃ — CH(CH₃)COOCH₃ 2-125 H S 0 H CF₂Cl CH₃ — CH(CH₃)COOC₂H₅ 2-126 H S 0 H CF₂ Cl CH₃ — CH(CH₃)COO^(n)C₃H₇2-127 H S 0 H CF₂ Cl CH₃ — CH(CH₃)COO^(n)C₄H₉ 2-128 H S 0 H CF₂ Cl CH₃ —CH(CH₃)COO^(n)C₅H₁₁ 2-129 H S 0 H CF₂Cl CH₃ — CH(CH₃)COO^(n)C₅H₁₁ 2-130H S 0 H CF₂Cl CH₃ — CH(CH₃)COO^(c)C₅H₉ 2-131 H S 0 H CF₂Cl CH₃ —CH(CH₃)COO^(c)C₆H₁₁ 2-132 F S 0 H CF₂Cl CH₃ — H 2-133 F S 0 H CF₂Cl CH₃— CH₃ 2-134 F S 0 H CF₂Cl CH₃ — C₂H₅ 2-135 F S 0 H CF₂Cl CH₃ — ^(n)C₃H₇2-136 F S 0 H CF₂Cl CH₃ — ^(n)C₄ ⁻H₉ 2-137 F S 0 H CF₂Cl CH₃ — ^(i)C₃H₇2-138 F S 0 H CF₂Cl CH₃ — ^(i)C₄H₉ 2-139 F S 0 H CF₂Cl CH₃ — CH₂CH₂Cl2-140 F S 0 H CF₂Cl CH₃ — CH₂CH₂Br 2-141 F S 0 H CF₂Cl CH₃ — CH₂CH═CH₂2-142 F S 0 H CF₂Cl CH₃ — CH(CH₃)CH ═CH₂ 2-143 F S 0 H CF₂Cl CH₃ —CH₂CCl═CH₂ 2-144 F S 0 H CF₂Cl CH₃ — CH₂C≡CH 2-145 F S 0 H CF₂Cl CH₃ —CH(CH₃)C≡CH 2-146 F S 0 H CF₂Cl CH₃ — CH₂CN 2-147 F S 0 H CF₂Cl CH₃ —CH₂OCH₃ 2-148 F S 0 H CF₂Cl CH₃ — CH₂OC₂H₅ 2-149 F S 0 H CF₂Cl CH₃ —CH₂COOH 2-150 F S 0 H CF₂Cl CH₃ — CH₂COOCH₃ 2-151 F S 0 H CF₂ Ci CH₃ —CH₂COOC₂ H₅ 2-152 F S 0 H CF₂Cl CH₃ — CH₂COO^(n)C₃H₇ 2-153 F S 0 H CF₂ClCH₃ — CH₂COO^(n)C₄H₉ 2-154 F S 0 H CF₂Cl CH₃ — CH₂COO^(n)C₅H₁₁ 2-155 F S0 H CF₂Cl CH₃ — CH₂COO^(i)C₃H₇ 2-156 F S 0 H CF₂Cl CH₃ — CH₂COO^(c)C₅H₉2-157 F S 0 H CF₂Cl CH₃ — CH₂COO^(c)C₆H₁₁ 2-158 F S 0 H CF₂Cl CH₃ —CH(CH₃)COOH 2-159 F S 0 H CF₂Cl CH₃ — CH(CH₃)COOCH₃ 2-160 F S 0 H CF₂ClCH₃ — CH(CH₃)COOC₂H₅ 2-161 F S 0 H CF₂Cl CH₃ — CH(CH₃)COO^(n)C₃H₇ 2-162F S 0 H CF₂Cl CH₃ — CH(CH₃)COO^(n)C₄H₉ 2-163 F S 0 H CF₂Cl CH₃ —CH(CH₃)COO^(n)C₅H₁₁ 2-164 F S 0 H CF₂Cl CH₃ — CH(CH₃)COO^(i)C₃H₇ 2-165 FS 0 H CF₂Cl CH₃ — CH(CH₃)COO^(c)C₅H₉ 2-166 F S 0 H CF₂Cl CH₃ —CH(CH₃)COO^(c)C₆H₁₁ 2-167 H O 0 H CF₂Cl CH₃ — H 2-168 H O 0 H CF₂Cl CH₃— CH₃ 2-169 H O 0 H CF₂Cl CH₃ — C₂H₅ 2-170 H O 0 H CF₂Cl CH₃ — ^(n)C₄H₉2-171 H O 0 H CF₂Cl CH₃ — ^(n)C₄H₉ 2-172 H O 0 H CF₂Cl CH₃ — ^(i)C₃H₇2-173 H O 0 H CF₂Cl CH₃ — ^(i)C₄H₉ 2-174 H O 0 H CF₂Cl CH₃ — CH₂CH═CH₂2-175 H O 0 H CF₂Cl CH₃ — CH(CH₃)CH═CH₂ 2-176 H O 0 H CF₂Cl CH₃ —CH₂C≡CH 2-177 H O 0 H CF₂Cl CH₃ — CH(CH₃)C≡CH 2-178 H O 0 H CF₂Cl CH₃ —CH₂OCH₃ 2-179 H O 0 H CF₂Cl CH₃ — CH₂OC₂H₅ 2-180 F O 0 H CF₂Cl CH₃ — H2-181 F O 0 H CF₂Cl CH₃ — CH₃ 2-182 F O 0 H CF₂Cl CH₃ — C₂H³¹ ₅ 2-183 FO 0 H CF₂Cl CH₃ — ^(n)C₃H₇ 2-184 F O 0 H CF₂Cl CF₃ — ^(n)C₄H₉ 2-185 F O0 H CF₂Cl CF₃ — CH₂CH═CH₂ 2-186 F O 0 H CF₂Cl CF₃ — CH(CH₃)CH═CH₂ 2-187F O 0 H CF₂Cl CH₃ — CH₂C≡CH 2-188 F O 0 H CF₂Cl CH₃ — CH(CH₃)C≡CH 2-189F O 0 H CF₂Cl CF₃ — CH₂OCH₃ 2-190 F O 0 H CF₂Cl CH₃ — CH₂OC₂H₅ 2-191 H O1 H CF₃ CH₃ — H 2-192 H O 1 H CF₃ CH₃ H CF₃ 2-193 H O 1 H CF₃ CH₃ H C₂H₅2-194 H O 1 H CF₃ CH₃ H ^(n)C₃H₇ 2-195 H O 1 H CF₃ CH₃ H ^(i)C₃H₇ 2-196H O 1 H CF₃ CH₃ H ^(i)C₄H₉ 2-197 H O 1 H CF₃ CH₃ H ^(n)C₄H₉ 2-198 H O 1H CF₂ CH₃ H CH₂CH₂Cl 2-199 H O 1 H CF₃ CH₃ H CH₂CH₂Br 2-200 H O 1 H CF₃CH₃ H CH₂CH═CH₂ 2-201 H O 1 H CF₃ CH₃ H CH(CH₃)CH═CH₂ 2-202 H O 1 H CF₃CH₃ H CH₂CCl═CH₂ 2-203 H O 1 H CF₃ CH₃ H CH₃C≡CH 2-204 H O 1 H CF₃ CH₃ HCH(CH₃)C≡CH 2-205 H O 1 H CF₃ CH₃ H CH₂CN⁻ 2-206 H O 1 H CF₃ CH₃ HCH₂OCH₃ 2-207 H O 1 H CF₃ CH₃ H CH₂OC₂H₅ 2-208 H O 1 H CF₃ CH₃ H CH₂COOH2-209 H O 1 H CF₃ CH₃ H CH₂COOCH₃ 2-210 H O 1 H CF₃ CH₃ H CH₂COOC₂H₅2-211 H O 1 H CF₃ CH₃ H CH₂COO^(n)C₃H₇ 2-212 H O 1 H CF₃ CH₃ HCH₂COO^(n)C₄H₉ 2-213 H O 1 H CF₃ CH₃ H CH₂COO^(n)C₅H₁₁ 2-214 H O 1 H CF₃CH₃ H CH₂COO^(i)C₃H₇ 2-215 H O 1 H CF₃ CH₃ H CH₂COO^(c)C₅H₉ 2-216 H O 1H CF₃ CH₃ H CH₂COO^(c)C₆H₁₁ 2-217 H O 1 H CF₃ CH₃ H CH(CH₃)COOH 2-218 HO 1 H CF₃ CH₃ H CH(CH₃)COOCH₃ 2-219 H O 1 H CF₃ CH₃ H CH(CH₃)COOC₂H₅2-220 H O 1 H CF₃ CH₃ H CH(CH₃)COO^(n)C₃H₇ 2-221 H O 1 H CF₃ CH₃ HCH(CH₃)COO^(n)C₄H₉ 2-222 H O 1 H CF₃ CH₃ H CH(CH₃)COO^(n)C₅H₁₁ 2-223 H O1 H CF₃ CH₃ H CH(CH₃)COO^(i)C₃H₇ 2-224 H O 1 H CF₃ CH₃ HCH(CH₃)COO^(c)C₅H₉ 2-225 H O 1 H CF₃ CH₃ H CH(CH₃)COO^(c)C₆H₁₁ 2-226 H O1 H CF₃ CH₃ CH₃ H 2-227 H O 1 H CF₃ CH₃ CH₃ CH₃ 2-228 H O 1 H CF₃ CH₃CH₃ C₂H₅ 2-229 H O 1 H CF₃ CH₃ CH₃ ^(n)C₃H₇ 2-230 H O 1 H CF₃ CH₃ CH₃^(i)C₃ H₇ 2-231 H O 1 H CF₃ CH₃ CH₃ ^(i)C₄ H₉ 2-232 H O 1 H CF₃ CH₃ CH₃^(n)C₄ H₉ 2-233 H O 1 H CF₃ CH₃ CH₃ CH₂CH═CH₂ 2-234 H O 1 H CF₃ CH₃ CH₃CH(CH₃)CH═CH₂ 2-235 H O 1 H CF₃ CH₃ CH₃ CH₂C≡CH 2-236 H O 1 H CF₃ CH₃CH₃ CH(CH₃)C≡CH 2-237 H O 1 H CF₃ CH₃ CH₃ CH₂OCH₃ 2-238 H O 1 H CF₃ CH₃CH₃ CH₂OC₂H₅ 2-239 F O 1 H CF₃ CH₃ H H 2-240 F O 1 H CF₃ CH₃ H CH₃ 2-241F O 1 H CF₃ CH₃ H C₂H₅ 2-242 F O 1 H CF₃ CH₃ H ^(n)C₃H₇ 2-243 F O 1 HCF₃ CH₃ H ^(i)C₃H₇ 2-244 F O 1 H CF₃ CH₃ H ^(i)C₄H₉ 2-245 F O 1 H CF₃CH₃ H ^(n)C₄H₉ 2-246 F O 1 H CF₃ CH₃ H CH₂CH₂Cl 2-247 F O 1 H CF₃ CH₃ HCH₂CH₂Br 2-248 F O 1 H CF₃ CH₃ H CH₂CH═CH₂ 2-249 F O 1 H CF₃ CH₃ HCH(CH₃)CH═CH₂ 2-250 F O 1 H CF₃ CH₃ H CH₂CCl³¹ ═CH₂ 2-251 F O 1 H CF₃CH₃ H CH₂C≡CH 2-252 F O 1 H CF₃ CH₃ H CH(CH₃)C≡CH 2-253 F O 1 H CF₃ CH₃H CH₂CN 2-254 F O 1 H CF₃ CH₃ H CH₂OCH₃ 2-255 F O 1 H CF₃ CH₃ H CH₂OC₂H₅2-256 F O 1 H CF₃ CH₃ H CH₂COOH 2-257 F O 1 H CF₃ CH₃ H CH₂COOCH 2-258 FO 1 H CF₃ CH₃ H CH₂COOC₂H₅ 2-259 F O 1 H CF₃ CH₃ H CH₂COO^(n)C₃H₇ 2-260F O 1 H CF₃ CH₃ H CH₂COO^(n)C₄H₉ 2-261 F O 1 H CF₃ CH₃ H CH₂COO^(n)C₅H₁₁2-262 F O 1 H CF₃ CH₃ H CH₂COO^(i)C₃H₇ 2-263 F O 1 H CF₃ CH₃ HCH₂COO^(C)C₅H₉ 2-264 F O 1 H CF₃ CH₃ H CH₂COO^(C)C₆H₁₁ 2-265 F O 1 H CF₃CH₃ H CH(CH₃)COOH 2-266 F O 1 H CF₃ CH₃ H CH(CH₃)COOCH₃ 2-267 F O 1 HCF₃ CH₃ H CH(CH₃)COOC₂H₅ 2-268 F O 1 H CF₃ CH₃ H CH(CH₃)COO^(n)C₃H₇2-269 F O 1 H CF₃ CH₃ H CH(CH₃)COO^(n)C₄H₉ 2-270 F O 1 H CF₃ CH₃ HCH(CH₃)COO^(n)C₅H₁₁ 2-271 F O 1 H CF₃ CH₃ H CH(CH₃)COO^(i)C₃H₇ 2-272 F O1 H CF₃ CH₃ H CH(CH₃)COO^(c)C₅H₉ 2-273 F O 1 H CF₃ CH₃ HCH(CH₃)COO^(c)C₆H₁₁ 2-274 F O 1 H CF₃ CH₃ CH₃ H 2-275 F O 1 H CF₃ CH₃CH₃ CH₃ 2-276 F O 1 H CF₃ CH₃ CH₃ C₂H₅ 2-277 F O 1 H CF₃ CH₃ CH₃^(n)C₃H₇ 2-278 F O 1 H CF₃ CH₃ CH₃ ^(i)C₃H₇ 2-279 F O 1 H CF₃ CH₃ CH₃^(i)C₄H₉ 2-280 F O 1 H CF₃ CH₃ CH₃ ^(n)C₄H₉ 2-281 F O 1 H CF₃ CH₃ CH₃CH₂CH═CH₂ 2-282 F O 1 H CF₃ CH₃ CH₃ CH(CH₃)CH═CH₂ 2-283 F O 1 H CF₃ CH₃CH₃ CH₂C≡CH 2-284 F O 1 H CF₃ CH₃ CH₃ CH(CH₃)C≡CH 2-285 F O 1 H CF₃ CH₃CH₃ CH₂OCH₃ 2-286 F O 1 H CF₃ CH₃ CH₃ CH₂OC₂H₅ 2-287 H S 0 H CF₃ CH₃ — H2-288 H S 0 H CF₃ CH₃ — CH₃ 2-289 H S 0 H CF₃ CH₃ — C₂H₅ 2-290 H S 0 HCF₃ CH₃ — ^(n)C₃H₇ 2-291 H S 0 H CF₃ CH₃ — ^(n)C₄H₉ 2-292 H S 0 H CF₃CH₃ — ^(i)C₃H₇ 2-293 H S 0 H CF₃ CH₃ — ^(i)C₄H₉ 2-294 H S 0 H CF₃ CH₃ —CH₂CH₂Cl 2-295 H S 0 H CF₃ CH₃ — CH₂CH₂Br 2-296 H S 0 H CF₃ CH₃ —CH₂CH═^(−CH) ₂ 2-297 H S 0 H CF₃ CH₃ — CH(CH₃)CH═CH₂ 2-298 H S 0 H CF₃CH₃ — CH₂CCl═CH₂ 2-299 H S 0 H CF₃ CH₃ — CH₂C≡CH 2-300 H S 0 H CF₃ CH₃ —CH(CH₃)C≡CH 2-301 H S 0 H CF₃ CH₃ — CH₂CN 2-302 H S 0 H CF₃ CH₃ —CH₂OCH₃ 2-303 H S 0 H CF₃ CH₃ — CH₂OC₂H₅ 2-304 H S 0 H CF₃ CH₃ — CH₂COOH2-305 H S 0 H CF₃ CH₃ — CH₂COOCH₃ 2-306 H S 0 H CF₃ CH₃ — CH₂COOC₂H₅2-307 H S 0 H CH₃ CH₃ — CH₂COO^(n)C₃H₇ 2-308 H S 0 H CF₃ CH₃ —CH₂COO^(n)C₄H₉ 2-309 H S 0 H CF₃ CH₃ — CH₂COO^(n)C₅H₁₁ 2-310 H S 0 H CF₃CH₃ — CH₂COO^(i)C₃H₇ 2-311 H S 0 H CF₃ CH₃ — CH₂COO^(c)C₆H₉ 2-312 H S 0H CF₃ CH₃ — CH₃COO^(c)C₆H₁₁ 2-313 H S 0 H CF₃ CH₃ — CH(CH₃)COOH 2-314 HS 0 H CF₃ CH₃ — CH(CH₃)COOCH₃ 2-315 H S 0 H CF₃ CH₃ — CfI(CH₃)COOC₂H₅2-316 H S 0 H CF₃ CH₃ — CH(CH₃)COO^(n)C₃H₇ 2-317 H S 0 H CF₃ CH₃ —CH(CH₃)COO^(n)C₄H₉ 2-318 H S 0 H CF₃ CH₃ — CH(CH₃)COO^(n)C₅H₁₁ 2-319 H S0 H CF₃ CH₃ — CH(CH₃)COO^(i)C₃H₇ 2-320 H S 0 H CF₃ CH₃ —CH(CH₃)COO^(c)C₅H₉ 2-321 H S 0 H CF₃ CH₃ — CH(CH₃)COO^(c)C₆H₁₁ 2-322 F S0 H CF₃ CH₃ — H 2-323 F S 0 H CF₃ CH₃ — CH₃ 2-324 F S 0 H CF₃ CH₃ — C₂H₅2-325 F S 0 H CF₃ CH₃ — ^(n)C₃H₇ 2-326 F 5 0 H CF₃ CH₃ — ^(n)C₄H₉ 2-327F S 0 H CF₃ CH₃ — ^(i)C₃H₇ 2-328 F 5 0 H CF₃ CH₃ — ⁵C₄H₉ 2-329 F 5 0 HCF₃ CH₃ — CH₂CH₂Cl 2-330 F S 0 H CF₃ CH₃ — CH₂CH₂Br 2-331 F S 0 H CF₃CH₃ — CH₂CH═CH₂ 2-332 F S 0 H CF₃ CH₃ — CH(CH₃)CH═CH₂ 2-333 F S 0 H CF₃CH₃ — CH₂CCl═CH₂ 2-334 F S 0 H CF₃ CH₃ — CH₂C≡CH 2-335 F S 0 H CF₃ CH₃ —CH(CH₃)C≡CH 2-336 F S 0 H CF₃ CH₃ — CH₂CN 2-337 F S 0 H CF₃ CH₃ —CH₂OCH₃ 2-338 F S 0 H CF₃ CH₃ — CH₂OC₂H₅ 2-339 F S 0 H CF₃ CH₃ — CH₂COOH2-340 F S 0 H CF₃ CH₃ — CH₂COOCH₃ 2-341 F S 0 H CF₃ CH₃ — CH₂COOC₂ ^(−H)₅ 2-342 F S 0 H CF₃ CH₃ — CH₂COO^(n)C₃H₇ 2-343 F S 0 H CF₃ CH₃ —CH₂COO^(n)C₄H₉ 2-344 F S 0 H CF₃ CH₃ — CH₂COO^(n)C₅H₁₁ 2-345 F S 0 H CF₃CH₃ — CH₂COO^(i)C₃H₇ 2-346 F S 0 H CF₃ CH₃ — CH₂COO^(c)C₅H₉ 2-347 F S 0H CF₃ CH₃ — CH₂COO^(c)C₆H₁₁ 2-348 F S 0 H CF₃ CH₃ — CH(CH₃)COOH 2-349 FS 0 H CF₃ CH₃ — CH(CH₃)COOCH₃ 2-350 F S 0 H CF₃ CH₃ — CH(CH₃)COOC₂H₅2-351 F S 0 H CF₃ CH₃ — CH(CH₃)COO^(n)C₃H₇ 2-352 F S 0 H CF₃ CH₃ —CH(CH₃)COO^(n)C₄H₉ 2-353 F S 0 H CF₃ CH₃ — CH(CH₃)COO^(n)C₆H₁₁ 2-354 F S0 H CF₃ CH₃ — CH(CH₃)COO^(i)C₃H₇ 2-355 F S 0 H CF₃ CH₃ —CH(CH₃)COO^(c)C₅H₉ 2-356 F S 0 H CF₃ CH₃ — CH(CH₃)COO^(c)C₆H₁₁ 2-357 H O0 H CF₃ CH₃ — H 2-358 H O 0 H CF₃ CH₃ — CH₃ 2-359 H O 0 H CF₃ CH₃ — C₂H₅2-360 H O 0 H CF₃ CH₃ — ^(n)C₃H₇ 2-361 H O 0 H CF₃ CH₃ — ^(n)C₄H₉ 2-362H O 0 H CF₃ CH₃ — ^(i)C₃H₇ 2-363 H O 0 H CF₃ CH₃ — ^(i)C₄H₉ 2-364 H O 0H CF₃ CH₃ — CH₂CH═⁻CH₂ 2-365 H O 0 H CF₃ CH₃ — CH(CH₃)CH═CH₂ 2-366 H O 0H CF₃ CH₃ — CH₂C≡CH 2-367 H O 0 H CF₃ CH₃ — CH(CH₃)C≡CH 2-368 H O 0 HCF₃ CH₃ — CH₂OCH₃ 2-369 H O 0 H CF₃ CH₃ — CH₂OC₂H₅ 2-370 F O 0 H CF₃ CH₃— H 2-371 F O 0 H CF₃ CH₃ — CH₃ 2-372 F O 0 H CF₃ CH₃ — C₂H₅ 2-373 F O 0H CF₃ CH₃ — ^(n)C₄H₇ 2-374 F O 0 H CF₃CH₃ — ^(n)C₄H₉ 2-375 F O 0 H CF₃CH₃ — CH₂CH═CH₂ 2-376 F O 0 H CF₃ CH₃ — CH(CH₃)CH═CH₂ 2-377 F O 0 H CF₃CH₃ — CH₂C≡CH 2-378 F O 0 H CF₃ CH₃ — CH(CH₃)C≡CH 2-379 F O 0 H CF₃ CH₃— CH₂OCH₃ 2-380 F O 0 H CF₃ CH₃ — CH₂OC₂H₅ 2-381 H O 1 H CF₂Cl H H H2-382 H O 1 H CF₂Cl H H CH₃ 2-383 H O 1 H CF₂Cl H H ^(n)C₂H₅ 2-384 H O 1H CF₂Cl H H ^(i)C₃H₇ 2-385 H O 1 H CF₂Cl H H ^(i)C₃H₇ 2-386 H O 1 HCF₂Cl H H ^(i)C₄H₉ 2-387 H O 1 H CF₂Cl H H ^(n)C₄ ⁻H₉ 2-388 H O 1 HCF₂Cl H H CH₂CH₂Cl 2-389 H O 1 H CF₂Cl H H CH₂CH₂Br 2-390 H O 1 H CF₂ClH H CH₂CH═CH₂ 2-391 H O 1 H CF₂Cl H H CH(CH₃)CH═CH₂ 2-392 H O 1 H CF₂ClH H CH₂CCl═CH₂ 2-393 H O 1 H CF₂Cl H H CH₂C≡CH 2-394 H O 1 H CF₂Cl H HCH(CH₃)C≡CH 2-395 H O 1 H CF₂Cl H H CH₂CN 2-396 H O 1 H CF₂Cl H HCH₂OCH₃ 2-397 H O 1 H CF₂Cl H H CH₂OC₂H₅ 2-398 H O 1 H CF₂Cl H H CH₂COOH2-399 H O 1 H CF₂Cl H H CH₂COOCH 2-400 H O 1 H CF₂Cl H H CH₂COOC₂H₅2-401 H O 1 H CF₂Cl H H CH₂COO^(n)C₃H₇ 2-402 H O 1 H CF₂Cl H HCH₂COO^(n)C₄H₉ 2-403 H O 1 H CF₂Cl H H CH₂COO^(n)C₅H₁₁ 2-404 H O 1 HCF₂Cl H H CH₂COO^(i)C₃H₇ 2-405 H O 1 H CF₂Cl H H CH₂COO^(c)C₅H₉ 2-406 HO 1 H CF₂Cl H H CH₂COO^(c)C₆H₁₁ 2-407 H O 1 H CF₂Cl H H CH(CH₃)COOH2-408 H O 1 H CF₂Cl H H CH(CH₃)COOCH₃ 2-409 H O 1 H CF₂Cl H HCH(CH₃)COOC₂H₅ 2-410 H O 1 H CF₂Cl H H CH(CH₃)COO^(n)C₃H₇ 2-411 H O 1 HCF₂Cl H H CH(CH₃)COO^(n)C₄H₉ 2-412 H O 1 H CF₂Cl H H CH(CH₃)COO^(n)C₅H₁₁2-413 H O 1 H CF₂Cl H H CH(CH₃)COO^(i)C₃H₇ 2-414 H O 1 H CF₂Cl H HCH(CH₃)COO^(c)C₅H₉ 2-415 H O 1 H CF₂Cl H H CH(CH₃)COO^(c)C₆H₁₁ 2-416 H O1 H CF₂Cl H CH₃ H 2-417 H O 1 H CF₂Cl H CH₃ CH₃ 2-418 H O 1 H CF₂Cl HCH₃ C₂H₅ 2-419 H O 1 H CF₂Cl H CH₃ ^(n)C₃H₇ 2-420 H O 1 H CF₂Cl H CH₃^(i)C₃H₇ 2-421 H O 1 H CF₂Cl H CH₃ ^(i)C₄H₉ 2-422 H O 1 H CF₂Cl H CH₃^(n)C₄H₉ 2-423 H O 1 H CF₂Cl H CH₃ CH₂ CH═CH₂ 2-424 H O 1 H CF₂Cl H CH₃CH(CH₃)CH═CH₂ 2-425 H O 1 H CF₂Cl H CH₃ CH₂C≡CH 2-426 H O 1 H CF₂Cl HCH₃ CH(CH₃)C≡CH 2-427 H O 1 H CF₂Cl H CH₃ CH₂OCH₃ 2-428 H O 1 H CF₂Cl HCH₃ CH₂OC₂H₅ 2-429 F O 1 H CF₂Cl H H H 2-430 F O 1 H CF₂ CL H H CH₃2-431 F O 1 H CF₂Cl H H C₂H₅ 2-432 F O 1 H CF₂Cl H H ^(n)C₃H₇ 2-433 F O1 H CF₂Cl H H ^(i)C₃ ^(−H) ₇ 2-434 F O 1 H CF₂Cl H H ^(i)C₄H₉ 2-435 F O1 H CF₂Cl H H ^(n)C₄H₉ 2-436 F O 1 H CF₂Cl H H CH₂CH₂Cl 2-437 F O 1 HCF₂Cl H H CH₂CH₂Br 2-438 F O 1 H CF₂Cl H H CH₂CH═CH₂ 2-439 F O 1 H CF₂ClH H CH(CH₃)CH═CH₂ 2-440 F O 1 H CF₂Cl H H CH₂CCl═CH₂ 2-441 F O 1 H CF₂ClH H CH₂C≡CH 2-442 F O 1 H CF₂Cl H H CH(CH₃)C≡CH 2-443 F O 1 H CF₂Cl H HCH₂CN 2-444 F O 1 H CF₂Cl H H CH₂OCH₃ 2-445 F O 1 H CF₂Cl H H CH₂OC₂H₅2-446 F O 1 H CF₂Cl H H CH₂COOH 2-447 F O 1 H CF₂Cl H H CH₂COOCH₃ 2-448F O 1 H CF₂Cl H H CH₂COOC₂H₅ 2-449 F O 1 H CF₂Cl H H CH₂COO^(n)C₃H₇2-450 F O 1 H CF₂Cl H H CH₂COO^(n)C₄H₉ 2-451 F O 1 H CF₂Cl H HCH₂COO^(n)C₅H₁₁ 2-452 F O 1 H CF₂Cl H H CH₂COO^(i)C₃H₇ 2-453 F O 1 HCF₂Cl H H CH₂COO^(c)C₅H₉ 2-454 F O 1 H CF₂Cl H H CH₂COO^(c)C₆H₁₁ 2-455 FO 1 H CF₂Cl H H CH(CH₃)COOH 2-456 F O 1 H CF₂Cl H H CH(CH₃)COOCH₃ 2-457F O 1 H CF₂Cl H H CH(CH₃)COOC₂H₅ 2-458 F O 1 H CF₂Cl H HCH(CH₃)COO^(n)C₃H₇ 2-459 F O 1 H CF₂Cl H H CH(CH₃)COO^(n)C₄H₉ 2-460 F O1 H CF₂Cl H H CH(CH₃)COO^(n)C₅H₁₁ 2-461 F O 1 H CF₂Cl H HCH(CH₃)COO^(i)C₃H₇ 2-462 F O 1 H CF₂Cl H H CH(CH₃)COO^(c)C₅H₉ 2-463 F O1 H CF₂Cl H H CH(CH₃)COO^(c)C₆H₁₁ 2-464 F O 1 H CF₂Cl H CH₃ H 2-465 F O1 H CF₂Cl H CH₃ CH₃ 2-466 F O 1 H CF₂Cl H CH₃ C₂H₅ 2-407 F O 1 H CF₂Cl HCH₃ ^(n)C₃H₇ 2-468 F O 1 H CF₂Cl H CH₃ ^(i)C₃H₇ 2-469 F O 1 H CF₂Cl HCH₃ ^(i)C₄H₉ 2-470 F O 1 H CF₂Cl H CH₃ ^(i)C₄H₉ 2-471 F O 1 H CF₂Cl HCH₃ CH₂CH═CH₂ 2-472 F O 1 H CF₂Cl H CH₃ CH(CH₃)CH═CH₂ 2-473 F O 1 HCF₂Cl H CH₃ CH₂C≡CH 2-474 F O 1 H CF₂Cl H CH₃ CH(CH₃)C≡CH 2-475 F O 1 HCF₂Cl H CH₃ CH₂OCH₃ 2-476 F O 1 H CF₂Cl H CH₃ CH₂OC₂H₅ 2-477 H S 0 HCF₂Cl H — H 2-478 H S 0 H CF₂Cl H — CH₃ ⁻ 2-479 H S 0 H CF₂Cl H — C₂H₅2-480 H S 0 H CF₂Cl H — ^(n)C₃H₇ 2-481 H S 0 H CF₂Cl H — ^(n)C₄H₉ 2-482H S 0 H CF₂Cl H — ^(n)C₃H₇ 2-483 H S 0 H CF₂Cl H — ^(i)C₄H₉ 2-484 H S 0H CF₂Cl H — CH₂CH₂Cl 2-485 H S 0 H CF₂Cl H — CH₂CH₂Br 2-486 H S 0 HCF₂Cl H — CH₂CH═CH₂ 2-487 H S 0 H CF₂Cl H — CH(CH₃)CH═CH₂ 2-488 H S 0 HCF₂Cl H — CH₂CCl═CH₂ 2-489 H S 0 H CF₂Cl H — CH₂C≡CH 2-490 H S 0 H CF₂ClH — CH(CH₃)C≡CH 2-491 H S 0 H CF₂Cl H — CH₂CN 2-492 H S 0 H CF₂Cl H —CH₂OCH₃ 2-493 H S 0 H CF₂Cl H — CH₂OC₂H₅ 2-494 H S 0 H CF₂ Cl H —CH₂COOH 2-495 H S 0 H CF₂ Cl H — CH₂COOCH₃ 2-496 H S 0 H CF₂ Cl H —CH₂COOC₂H₅ 2-497 H S 0 H CF₂ Cl H — CH₂COO^(n)C₃H₇ 2-498 H S 0 H CF₂ ClH — CH₂COO^(n)C₄H₉ 2-499 H S 0 H CF₂ Cl H — CH₂COOC^(n)C₅H₁₁ 2-500 H S 0H CF₂ Cl H — CH₂COO^(i)C₃H₇ 2-501 H S 0 H CF₂ Cl H — CH₂COO^(c) ⁻ C₅H₉2-502 H S 0 H CF₂ Cl H — CH₂COO^(c)C₆H₁₁ 2-503 H S 0 H CF₂ Cl H —CH(CH₃)COOH 2-504 H S 0 H CF₂ Cl H — CH(CH₃)COOCH₃ 2-505 H S 0 H CF₂ ClH — CH(CH₃)COOC₂H₅ 2-506 H S 0 H CF₂ Cl H — CH(CH₃)COO^(n)C₃H₇ 2-507 H S0 H CF₂ Cl H — CH(CH₃)COO^(n)C₄H₉ 2-508 H S 0 H CF₂ Cl H —CH(CH₃)COO^(n)C₄H₁₁ 2-509 H S 0 H CF₂ Cl H — CH(CH₃)COO^(i)C₃H₇ 2-510 HS 0 H CF₂ Cl H — CH(CH₃)COO^(c)C₅H₉ 2-511 H S 0 H CF₂ Cl H —CH(CH₃)COO^(c)C₆H₁₁ 2-512 F S 0 H CF₂ Cl H — H 2-513 F S 0 H CF₂ Cl H —CH₃ 2-514 F S 0 H CF₂ Cl H — C₂H₅ 2-515 F S 0 H CF₂ Cl H — ^(n)C₃H₇2-516 F S 0 H CF₂ Cl H — ^(n)C₄H₉ 2-517 F S 0 H CF₂Cl H — ^(i)C₃H₇ 2-518F S 0 H CF₂Cl H — ^(i)C₄H₉ 2-519 F S 0 H CF₂Cl H — CH₂CH₂Cl 2-520 F S 0H CF₂Cl H — CH₂CH₂Br 2-521 F S 0 H CF₂Cl H — CH₂CH═CH₂ 2-522 F S 0 HCF₂Cl H — CH(CH₃)CH═CH₂ 2-523 F S 0 H CF₂Cl H — CH₂CCl═CH₂ 2-524 F S 0 HCF₂Cl H — CH₂C≡CH 2-525 F S 0 H CF₂Cl H — CH(CH₃)C≡CH 2-526 F 5 0 HCF₂Cl H — CH₂CN 2-527 F S 0 H CF₂Cl H — CH₂OCH₃ 2-528 F S 0 H CF₂Cl H —CH₂OC₂H₅ 2-529 F S 0 H CF₂Cl H — CH₂COOH 2-530 F S 0 H CF₂Cl H —CH₂COOCH₃ 2-531 F 5 0 H CF₂Cl H — CH₂COOC₂H₅ 2-532 F S 0 H CF₂Cl H —CH₂COO^(n)C₃H₇ 2-533 F S 0 H CF₂Cl H — CH₂COO^(n)C₄H₉ 2-534 F S 0 HCF₂Cl H — CH₂COO^(n)C₅H₁₁ 2-535 F S 0 H CF₂Cl H — CH₂COO^(i)C₃H₇ 2-536 FS 0 H CF₂Cl H — CH₂COO^(c)C₅H₉ 2-537 F S 0 H CF₂Cl H — CH₂COO^(c)C₆H₁₁2-538 F S 0 H CF₂Cl H — CH(CH₃)COOH 2-539 F S 0 H CF₂Cl H —CH(CH₃)COOCH₃ 2-540 F S 0 H CF₂Cl H — CH(CH₃)COOC₂H₅ 2-541 F S 0 H CF₂ClH — CH(CH₃)COO^(n)C₃H₇ 2-542 F S 0 H CF₂Cl H — CH(CH₃)COO^(n)C₄H₉ 2-543F S 0 H CF₂Cl H — CH(CH₃)COO^(n)C₅H₁₁ 2-544 F S 0 H CF₂Cl H —CH(CH₃)COO^(i)C₃H₇ 2-545 F S 0 H CF₂Cl H — CH(CH₃)COO^(c)C₅H₉ 2-546 F S0 H CF₂Cl H — CH(CH₃)COO^(c)C₆H₁₁ 2-547 H O 0 H CF₂Cl H — H⁻ 2-548 H O 0H CF₂Cl H — CH₃ 2-549 H O 0 H CF₂Cl H — C₂H₅ 2-550 H O 0 H CF₂Cl H —^(n)C₃H₇ 2-551 H O 0 H CF₂Cl H — ^(n)C₄H₉ 2-552 H O 0 H CF₂Cl H —^(i)C₃H₇ 2-553 H O 0 H CF₂Cl H — ^(i)C₄H₉ 2-554 H O 0 H CF₂Cl H —CH₂CH═CH₂ 2-555 H O 0 H CF₂Cl H — CH(CH₃)CH═CH₂ 2-556 H O 0 H CF₂Cl H —CH₂C≡CH 2-557 H O 0 H CF₂Cl H — CH(CH₃)C≡CH 2-558 H O 0 H CF₂Cl H —CH₂OCH₃ 2-559 H O 0 H CF₂Cl H — CH₂OC₂H₃ 2-560 F O 0 H CF₂Cl H — H 2-561F O 0 H CF₂Cl H — CH₃ 2-562 F O 0 H CF₂Cl H — C₂H₅ 2-563 F O 0 H CF₂Cl H— ^(n)C₃H₇ 2-564 F O 0 H CF₂Cl H — ^(n)C₄H₉ 2-565 F O 0 H CF₂Cl H —CH₂CH═CH₂ 2-566 F O 0 H CF₂ C1 H — CH(CH₃)CH═CH₂ 2-567 F O 0 H CF₂ C1 H— CH₂C≡CH 2-568 F O 0 H CF₂Cl H — CH(CH₃)C≡CH 2-569 F O 0 H CF₂Cl H —CH₂OCH⁻ ₃ 2-570 F O 0 H CF₂Cl H — CH₂OC₂H₅ 2-571 H O 1 H CF₃ H H H 2-572H O 1 H CF₃ H H CH₃ 2-573 H O 1 H CF₃ H H C₂H₅ 2-574 H O 1 H CF₃ H H^(n)C₃H₇ 2-575 H O 1 H CF₃ H H ^(i)C₃H₇ 2-576 H O 1 H CF₃ H H ^(i)C₄H₉2-577 H O 1 H CF₃ H H ^(n)C₄H₉ 2-578 H O 1 H CF₃ H H CH₂CH₂Cl 2-579 H O1 H CF₃ H H CH₂CH₂Br 2-580 H O 1 H CF₃ H H CH₂CH═CH₂ 2-581 H O 1 H CF₃ HH CH(CH₃)CH═CH₂ 2-582 H O 1 H CF₃ H H CH₂CCl═CH₂ 2-583 H O 1 H CF₃ H HCH₂C≡CH 2-584 H O 1 H CF₃ H H CH(CH₃)C≡CH 2-585 H O 1 H CF₃ H H CH₂CN2-586 H O 1 H CF₃ H H CH₂OCH₃ 2-587 H O 1 H CF₃ H H CH₂OC₂H₅ 2-588 H O 1H CF₃ H H CH₂COOH 2-589 H O 1 H CF₃ H H CH₂COOCH₃ 2-590 H O 1 H CF₃ H HCH₂COOC₂H₅ 2-591 H O 1 H CF₃ H H CH₂COO^(n)C₃H₇ 2-592 H O 1 H CF₃ H HCH₂COO^(n) ⁻ C₄H₉ 2-593 H O 1 H CF₃ H H CH₂COO^(n)C₅H₁₁ 2-594 H O 1 HCF₃ H H CH₂COO^(i)C₃H₇ 2-595 H O 1 H CF₃ H H CH₂COO^(c)C₅H₉ 2-596 H O 1H CF₃ H H CH₂COO^(c)C₆H₁₁ 2-597 H O 1 H CF₃ H H CH(CH₃)COOH 2-598 H O 1H CF₃ H H CH(CH₃)COOCH₃ 2-599 H O 1 H CF₃ H H CH(CH₃)COOC₂H₅ 2-60O H O 1H CF₃ H H CH(CH₃)COO^(c)C₃H₇ 2-601 H O 1 H CF₃ H H CH(CH₃)COO^(c)C₄H₉2-602 H O 1 H CF₃ H H CH(CH₃)COO^(c)C₅H₁₁ 2-603 H O 1 H CF₃ H HCH(CH₃)COO^(i)C₃H₇ 2-604 H O 1 H CF₃ H H CH(CH₃)COO^(c)C₅H₉ 2-605 H O 1H CF₃ H H CH(CH₃)COO^(c)C₆H₁₁ 2-606 H O 1 H CF₃ H CH₃ H 2-607 H O 1 HCF₃ H CH₃ CH₃ 2-608 H O 1 H CF₃ H CH₃ C₂H₅ 2-609 H O 1 H CF₃ H CH₃^(n)C₃H₇ 2-610 H O 1 H CF₃ H CH₃ ^(i)C₃H₇ 2-611 H O 1 H CF₃ H CH₃^(i)C₄H₉ 2-612 H O 1 H CF₃ H CH₃ ^(n)C₄H₉ 2-613 H O 1 H CF₃ H CH₃CH₂CH═CH₂ 2-614 H O 1 H CF₃ H CH₃ CH(CH₃)CH═CH₂ 2-615 H O 1 H CF₃ H CH₃CH₂C≡⁻CH 2-616 H O 1 H CF₃ H CH₃ CH(CH₃)C≡CH 2-617 H O 1 H CF₃ H CH₃CH₂OCH₃ 2-618 H O 1 H CF₃ H CH₃ CH₂OC₂H₅ 2-619 F O 1 H CF₃ H H H 2-620 FO 1 H CF₃ H H CH₃ 2-621 F O 1 H CF₃ H H C₂H₅ 2-622 F O 1 H CF₃ H H C₂H₅2-623 F O 1 H CF₃ H H ^(i)C₃H₇ 2-624 F O 1 H CF₃ H H ^(i)C₄H₉ 2-625 F O1 H CF₃ H H ^(n)C₄H₉ 2-626 F O 1 H CF₃ H H CH₂CH₂Cl 2-627 F O 1 H CF₃ HH CH₂CH₂Br 2-628 F O 1 H CF₃ H H CH₂CH═CH₂ 2-629 F O 1 H CF₃ H HCH(CH₃)CH═CH₂ 2-630 F O 1 H CF₃ H H CH₂CCl═CH₂ 2-631 F O 1 H CF₃ H HCH₂C≡CH 2-632 F O 1 H CF₃ H H CH(CH₃)C≡CH 2-633 F O 1 H CF₃ H H CH₂CN2-634 F O 1 H CF₃ H H CH₂OCH₃ 2-635 F O 1 H CF₃ H H CH₂OC₂H₅ 2-636 F O 1H CF₃ H H CH₂COOH 2-637 F O 1 H CF₃ H H CH₂COOCH₃ 2-638 F O 1 H CF₃ H HCH₂COOC₂ ⁻H₅ 2-639 F O 1 H CF₃ H H CH₂COO^(n)C₃H₇ 2-640 F O 1 H CF₃ H HCH₂COO^(n)C₄H₉ 2-641 F O 1 H CF₃ H H CH₂COO^(n)C₅H₁₁ 2-642 F O 1 H CF₃ HH CH₂COO^(i)C₃H₇ 2-643 F O 1 H CF₃ H H CH₂COO^(c)C₅H₉ 2-644 F O 1 H CF₃H H CH₂COO^(c)C₆H₁₁ 2-645 F O 1 H CF₃ H H CH(CH₃)COOH 2-646 F O 1 H CF₃H H CH(CH₃)COOCH₃ 2-647 F O 1 H CF₃ H H CH(CH₃)COOC₂H₅ 2-648 F O 1 H CF₃H H CH(CH₃)COO^(n)C₃H₇ 2-648 F O 1 H CF₃ H H CH(CH₃)COO^(n)C₄H₉ 2-650 FO 1 H CF₃ H H CH(CH₃)COO^(n)C₅H₁₁ 2-651 F O 1 H CF₃ H HCH(CH₃)COO^(i)C₃H₇ 2-652 F O 1 H CF₃ H H CH(CH₃)COO^(c)C₅H₉ 2-653 F O 1H CF₃ H H CH(CH₃)COO^(c)C₆H₁₁ 2-654 F O 1 H CF₃ H CH₃ H 2-655 F O 1 HCF₃ H CH₃ CH₃ 2-656 F O 1 H CF₃ H CH₃ C₂H₅ 2-657 F O 1 H CF₃ H CH₃^(n)C₃H₇ 2-658 F O 1 H CF₃ H CH₃ ^(i)C₃H₇ 2-659 F O 1 H CF₃ H CH₃^(i)C₄H₉ 2-660 F O 1 H CF₃ H CH₃ ^(n)C₄H₉ 2-661 F O 1 H CF₃ H CH₃CH₂CH═⁻CH₂ 2-662 F O 1 H CF₃ H CH₃ CH(CH₃)CH═CH₂ 2-663 F O 1 H CF₃ H CH₃CH₂C≡CH 2-664 F O 1 H CF₃ H CH₃ CH(CH₃)C≡CH 2-665 F O 1 H CF₃ H CH₃CH₂OCH₃ 2-666 F O 1 H Ch H CH₃ CH₂OC₂H₅ 2-667 H S 0 H CF₃ H — H 2-668 HS 0 H CF₃ H — CH₃ 2-669 H S 0 H CF₃ H — C₂H₅ 2-670 H S 0 H CF₃ H —^(n)C₃H₇ 2-671 H S 0 H CF₃ H — ^(n)C₄H₉ 2-672 H S 0 H CF₃ H — ^(i)C₃H₇2-673 H S 0 H CF₃ H — ^(i)C₄H₉ 2-674 H S 0 H CF₃ H — CH₂CH₂Cl 2-675 H S0 H CF₃ H — CH₂CH₂Br 2-676 H S 0 H CF₃ H — CH₂CH═CH₂ 2-677 H S 0 H CF₃ H— CH(CH₃)CH═CH₂ 2-678 H S 0 H CF₃ H — CH₂CCl═CH₂ 2-679 H S 0 H CF₃ H —CH₂C≡CH 2-680 H S 0 H CF₃ H — CH(CH₃)C≡CH 2-681 H S 0 H CF₃ H — CH₂CN2-682 H S 0 H CF₃ H — CH₂OCH₃ 2-683 H S 0 H CF₃ H — CH₂OC₂ ⁻H₅ 2-684 H S0 H CF₃ H — CH₂COOH 2-685 H S 0 H CF₃ H — CH₂COOCH₃ 2-686 H S 0 H CF₃ H— CH₂COOC₂H₅ 2-687 H S 0 H CF₃ H — CH₂COO^(n)C₃H₇ 2-688 H S 0 H CF₃ H —CH₂COO^(n)C₄H₉ 2-689 H S 0 H CF₃ H — CH₂COO^(n)C₅H₁₁ 2-690 H S 0 H CF₃ H— CH₂COO^(i)C₃H₇ 2-691 H S 0 H CF₃ H — CH₂COO^(c)C₅H₉ 2-692 H S 0 H CF₃H — CH₂COO^(c)C₆H₁₁ 2-693 H S 0 H CF₃ H — CH(CH₃)COOH 2-694 H S 0 H CF₃H — CH(CH₃)COOCH₃ 2-695 H S 0 H CF₃ H — CH(CH₃)COOC₂H₅ 2-696 H S 0 H CF₃H — CH(CH₃)COO^(n)C₃H₇ 2-697 H S 0 H CF₃ H — CH(CH₃)COO^(n)C₄H₉ 2-698 HS 0 H CF₃ H — CH(CH₃)COO^(n)C₅H₁₁ 2-699 H S 0 H CF₃ H—CH(CH₃)COO^(i)C₃H₇ 2-700 H S 0 H CF₃ H— CH(CH₃)COO^(c)C₅H₉ 2-701 H S 0 HCF₃ H— CH(CH₃)COO^(c)C₆H₁₁ 2-702 F S 0 H CF₃ H — H 2-703 F S 0 H CF₃ H —CH₃ 2-704 F S 0 H CF₃ H — C₂H₅ 2-705 F S 0 H CF₃ H — ^(n)C₃H₁₁ 2-706 F S0 H CF₃ H — ^(n)C₄ ⁻H₉ 2-707 F S 0 H CF₃ H — ^(i)C₃H₇ 2-708 F S 0 H CF₃H — ^(s)C₄H₉ 2-709 F S 0 H CF₃ H — CH₂CH₂Cl 2-710 F S 0 H CF₃ H —CH₂CH₂Br 2-711 F S 0 H CF₃ H — CH₂CH═CH₂ 2-712 F S 0 H CF₃ H —CH(CH₃)CH═CH₂ 2-713 F S 0 H CF₃ H — CH₂CCl═CH₂ 2-714 F S 0 H CF₃ H —CH₂C≡CH 2-715 F S 0 H CF₃ H — CH(CH₃)C≡CH 2-716 F S 0 H CF₃ H — CH₂CN2-717 F S 0 H CF₃ H — CH₂OCH₃ 2-718 F S 0 H CF₃ H — CH₂OC₂H₅ 2-719 F S 0H CF₃ H — CH₂COOH 2-720 F S 0 H CF₃ H — CH₂COOCH₃ 2-721 F S 0 H CF₃ H —CH₂COOC₂H₅ 2-722 F S 0 H CF₃ H — CH₂COO^(n)C₃H₇ 2-723 F S 0 H CF₃ H —CH₂COO^(n)C₄H₉ 2-724 F S 0 H CF₃ H — CH₂COO^(n)C₅H₁₁ 2-725 F S 0 H CF₃ H— CH₂COO^(i)C₃H₇ 2-726 F S 0 H CF₃ H — CH₂COO^(c)C₅H₉ 2-727 F S 0 H CF₃H — CH₂COO^(c)C₆H₁₁ 2-728 F S 0 H CF₃ H — CH(CH₃)COOH 2-729 F S 0 H CF₃H — CH(CH₃)COOCH₃ 2-730 F S 0 H CF₃ H — CH(CH₃)COOC₂H₅ 2-731 F S 0 H CF₃H — CH(CH₃)COO^(n)C₃H₇ 2-732 F S 0 H CF₃ H — CH(CH₃)COO^(n)C₄H₉ 2-733 FS 0 H CF₃ H — CH(CH₃)COO^(n)C₅H₁₁ 2-734 F S 0 H CF₃ H —CH(CH₃)COO^(i)C₃H₇ 2-735 F S 0 H CF₃ H — CH(CH₃)COO^(c)C₅H₉ 2-736 F S 0H CF₃ H — CH(CH₃)COO^(c)C₆H₁₁ 2-737 H O 0 H CF₃ H — H 2-738 H O 0 H CF₃H — CH₃ 2-739 H O 0 H CF₃ H — C₂H₅ 2-740 H O 0 H CF₃ H — ^(n)C₃H₇ 2-741H O 0 H CF₃ H — ^(n)C₄H₉ 2-742 H O 0 H CF₃ H — ^(i)C₃H₇ 2-743 H O 0 HCF₃ H — ^(i)C₄H₉ 2-744 H O 0 H CF₃ H — CH₂CH═CH₂ 2-745 H O 0 H CF₃ H —CH(CH₃)CH═CH₂ 2-746 H O 0 H CF₃ H — CH₂C≡CH 2-747 H O 0 H CF₃ H —CH(CH₃)C≡CH 2-748 H O 0 H CF₃ H — CH₂OCH₃ 2-749 H O 0 H CF₃ H — CH₂OC₂H₅2-750 F O 0 H CF₃ H — H 2-751 F O 0 H CF₃ H — CH₃ 2-752 F O 0 H CF₃ H —C₂H⁻ ₅ 2-753 F O 0 H CF₃ H — ^(n)C₃H₇ 2-754 F O 0 H CF₃ H — ^(n)C₄H₉2-755 F O 0 H CF₃ H — CH₂CH═CH₂ 2-756 F O 0 H CF₃ H — CH(CH₃)CH═CH₂2-757 F O 0 H CF₃ H — CH₂C≡CH 2-758 F O 0 H CF₃ H — CH(CH₃)C≡CH 2-759 FO 0 H CF₃ H — CH₂OCH₃ 2-760 F O 0 H CF₃ H — CH₂OC₂H₅ 2-761 H O 1 CH₃ CF₃H H H 2-762 H O 1 CH₃ CF₃ H H CH₃ 2-763 H O 1 CH₃ CF₃ H H C₂H₅ 2-764 H O1 CH₃ CF₃ H H ^(n)C₃H₇ 2-765 H O 1 CH₃ CF₃ H H ^(i)C₃H₇ 2-766 H O 1 CH₃CF₃ H H ^(i)C₄H₉ 2-767 H O 1 CH₃ CF₃ H H ^(n)C₄H₉ 2-768 H O 1 CH₃ CF₃ HH CH₂CH₂Cl 2-769 H O 1 CH₃ CF₃ H H CH₂CH₂Br 2-770 H O 1 CH₃ CF₃ H HCH₂CH═CH₂ 2-771 H O 1 CH₃ CF₃ H H CH(CH₃)CH═CH₂ 2-772 H O 1 CH₃ CF₃ H HCH₂CCl═CH₂ 2-773 H O 1 CH₃ CF₃ H H CH₂C≡CH 2-774 H O 1 CH₃ CF₃ H HCH(CH₃)C≡CH 2-775 H O 1 CH₃ CF₃ H H CH₂CN⁻ 2-776 H O 1 CH₃ CF₃ H HCH₂OCH₃ 2-777 H O 1 CH₃ CF₃ H H CH₂OC₂H₅ 2-778 H O 1 CH₃ CF₃ H H CH₂COOH2-779 H O 1 CH₃ CF₃ H H CH₂COOCH₃ 2-780 H O 1 CH₃ CF₃ H H CH₂COOC₂H₅2-781 H O 1 CH₃ CF₃ H H CH₂COO^(n)C₃H₇ 2-782 H O 1 CH₃ CF₃ H HCH₂COO^(n)C₄H₉ 2-783 H O 1 CH₃ CF₃ H H CH₂COO^(n)C₅H₁₁ 2-784 H O 1 CH₃CF₃ H H CH₂COO^(i)C₃H₇ 2-785 H O 1 CH₃ CF₃ H H CH₂COO^(c)C₆H₉ 2-786 H O1 CH₃ CF₃ H H CH₂COO^(c)C₆H₁₁ 2-787 H O 1 CH₃ CF₃ H H CH(CH₃)COOH 2-788H O 1 CH₃ CF₃ H H CH(CH₃)COOCH₃ 2-789 H O 1 CH₃ CF₃ H H CH(CH₃)COOC₂H₅2-790 H O 1 CH₃ CF₃ H H CH(CH₃)COO^(n)C₃H₇ 2-791 H O 1 CH₃ CF₃ H HCH(CH₃)COO^(n)C₄H₉ 2-792 H O 1 CH₃ CF₃ H H CH(CH₃)COO^(n)C₅H₁₁ 2-793 H O1 CH₃ CF₃ H H CH(CH₃)COO^(i)C₃H₇ 2-794 H O 1 CH₃ CF₃ H HCH(CH₃)COO^(c)C₅H₉ 2-795 H O 1 CH₃ CF₃ H H CH(CH₃)COO^(c)C₆H₁₁ 2-796 H O1 CH₃ CF₃ H CH₃ H 2-797 H O 1 CH₃ CF₃ H CH₃ CH₃ ⁻ 2-798 H O 1 CH₃ CF₃ HCH₃ C₂H₅ 2-799 H O 1 CH₃ CF₃ H CH₃ ^(n)C₃H₇ 2-800 H O 1 CH₃ CF₃ H CH₃^(i)C₃H₇ 2-801 H O 1 CH₃ CF₃ H CH₃ ^(i)C₄H₉ 2-802 H O 1 CH₃ CF₃ H CH₃^(n)C₄H₉ 2-803 H O 1 CH₃ CF₃ H CH₃ CH₂CH═CH₂ 2-804 H O 1 CH₃ CF₃ H CH₃CH(CH₃)CH═CH₂ 2-805 H O 1 CH₃ CF₃ H CH₃ CH₂C≡CH 2-806 H O 1 CH₃ CF₃ HCH₃ CH(CH₃)C≡CH 2-807 H O 1 CH₃ CF₃ H CH₃ CH₂OCH₃ 2-808 H O 1 CH₃ CF₃ HCH₃ CH₂OC₂H₅ 2-809 F O 1 CH₃ CF₃ H H H 2-810 F O 1 CH₃ CF₃ H H CH₃ 2-811F O 1 CH₃ CF₃ H H C₂H₅ 2-812 F O 1 CH₃ CF₃ H H ^(n)C₃H₇ 2-813 F O 1 CH₃CF₃ H H ^(i)C₃H₇ 2-814 F O 1 CH₃ CF₃ H H ^(i)C₄H₉ 2-815 F O 1 CH₃ CF₃ HH ^(n)C₄H₉ 2-816 F O 1 CH₃ CF₃ H H CH₂CH₂Cl 2-817 F O 1 CH₃ CF₃ H HCH₂CH₂Br 2-818 F O 1 CH₃ CF₃ H H CH₂CH═CH₂ 2-819 F O 1 CH₃ CF₃ H HCH(CH₃)CH═CH₂ 2-820 F O 1 CH₃ CF₃ H H CH₂CCl^(−═CH) ₂ 2-821 F O 1 CH₃CF₃ H H CH₂C≡CH 2-822 F O 1 CH₃ CF₃ H H CH(CH₃)C≡CH 2-823 F O 1 CH₃ CF₃H H CH₂CN 2-824 F O 1 CH₃ CF₃ H H CH₂OCH₃ 2-825 F O 1 CH₃ CF₃ H HCH₂OC₂H₅ 2-826 F O 1 CH₃ CF₃ H H CH₂COOH 2-827 F O 1 CH₃ CF₃ H HCH₂COOCH₃ 2-828 F O 1 CH₃ CF₃ H H CH₂COOC₂H₅ 2-829 F O 1 CH₃ CF₃ H HCH₂COO^(n)C₃H₇ 2-830 F O 1 CH₃ CF₃ H H CH₂COO^(n)C₄H₉ 2-831 F O 1 CH₃CF₃ H H CH₂COO^(n)C₅H₁₁ 2-832 F O 1 CH₃ CF₃ H H CH₂COO^(i)C₃H₇ 2-833 F O1 CH₃ CF₃ H H CH₂COO^(c)C₅H₉ 2-834 F O 1 CH₃ CF₃ H H CH₂COO^(c)C₆H₁₁2-835 F O 1 CH₃ CF₃ H H CH(CH₃)COOH 2-836 F O 1 CH₃ CF₃ H HCH(CH₃)COOCH₃ 2-837 F O 1 CH₃ CF₃ H H CH(CH₃)COOC₂H₅ 2-838 F O 1 CH₃ CF₃H H CH(CH₃)COO^(n)C₃H₇ 2-839 F O 1 CH₃ CF₃ H H CH(CH₃)COO^(n)C₄H₉ 2-840F O 1 CH₃ CF₃ H H CH(CH₃)COO^(n)C₅H11 2-841 F O 1 CH₃ CF₃ H HCH(CH₃)COO^(i)C₃H₇ 2-842 F O 1 CH₃ CF₃ H H CH(CH₃)COO^(c)C₅H₉ 2-843 F O1 CH₃ CF₃ H H CH(CH₃)COO^(c)C₆H₁₁ 2-843 F O 1 CH₃ CF₃ H CH₃ H 2-845 F O1 CH₃ CF₃ H CH₃ CH₃ 2-846 F O 1 CH₃ CF₃ H CH₃ C₂H₅ 2-847 F O 1 CH₃ CF₃ HCH₃ ^(n)C₃H₇ 2-848 F O 1 CH₃ CF₃ H CH₃ ^(i)C₃H₇ 2-849 F O 1 CH₃ CF₃ HCH₃ ^(i)C₄H₉ 2-850 F O 1 CH₃ CF₃ H CH₃ ^(n)C₄H₉ 2-851 F O 1 CH₃ CF₃ HCH₃ CH₂CH═CH₂ 2-852 F O 1 CH₃ CF₃ H CH₃ CH(CH₃)CH═CH₂ 2-853 F O 1 CH₃CF₃ H CH₃ CH₂C≡CH 2-854 F O 1 CH₃ CF₃ H CH₃ CH(CH₃)C≡CH 2-855 F O 1 CH₃CF₃ H CH₃ CH₂OCH₃ 2-856 F O 1 CH₃ CF₃ H CH₃ CH₂OC₂H₅ 2-857 H S 0 CH₃ CF₃H — H 2-858 H S 0 CH₃ CF₃ H — CH₃ 2-859 H S 0 CH₃ CF₃ H — C₂H₅ 2-860 H S0 CH₃ CF₃ H — ^(n)C₃H₇ 2-861 H S 0 CH₃ CF₃ H — ^(n)C₄H₉ 2-862 H S 0 CH₃CF₃ H — ^(i)C₃H₇ 2-863 H S 0 CH₃ CF₃ H — ^(i)C₄H₉ 2-864 H S 0 CH₃ CF₃ H— CH₂CH₂Cl 2-865 H S 0 CH₃ CF₃ H — CH₂CH₂Br 2-866 H S 0 CH₃ CF₃ H —CH₂CH═⁻CH₂ 2-867 H S 0 CH₃ CF₃ H — CH(CH₃)CH═CH₂ 2-868 H S 0 CH₃ CF₃ H —CH₂CCl═CH₂ 2-869 H S 0 CH₃ CF₃ H — CH₂C≡CH 2-870 H S 0 CH₃ CF₃ H —CH(CH₃)C≡CH 2-871 H S 0 CH₃ CF₃ H — CH₂CN 2-872 H S 0 CH₃ CF₃ H —CH₂OCH₃ 2-873 H S 0 CH₃ CF₃ H — CH₂OC₂H₅ 2-874 H S 0 CH₃ CF₃ H —CH₂COOH₃ 2-875 H S 0 CH₃ CF₃ H — CH₂COOCH₃ 2-876 H S 0 CH₃ CF₃ H —CH₂COOC₂H₅ 2-877 H S 0 CH₃ CF₃ H — CH₂COO^(n)C₃H₇ 2-878 H S 0 CH₃ CF₃ H— CH₂COO^(n)C₄H₉ 2-879 H S 0 CH₃ CF₃ H — CH₂COO^(n)C₆H₁₁ 2-880 H S 0CH₃CF₃ H — CH₂COO^(i)C₃H₇ 2-881 H S 0 CH₃CF₃ H — CH₂COO^(c)C₅H₉ 2-882 HS 0 CH₃ CF₃ H — CH₂COO^(c)C₆H₁₁ 2-883 H S 0 CH₃ CF₃ H — CH(CH₃)COOH2-884 H S 0 CH₃ CF₃ H — CH(CH₃)COOCH₃ 2-885 H S 0 CH₃ CF₃ H —CH(CH₃)COOC₂H₅ 2-886 H S 0 CH₃ CF₃ H — CH(CH₃)COO^(n)C₃H₇ 2-887 H S 0CH₃ CF₃ H — CH(CH₃)COO^(n)C₄H₉ 2-888 H S 0 CH₃ CF₃ H —CH(CH₃)COO^(n)C₅H₁₁ 2-889 H S 0 CH₃ CF₃ H — CH(CH₃)COO^(i)C₃H₇ 2-890 H S0 CH₃ CF₃ H — CH(CH₃)COO^(c)C₅H₉ 2-891 H S 0 CH₃ CF₃ H —CH(CH₃)COO^(c)C₆H₁₁ 2-892 F S 0 CH₃ CF₃ H — H 2-893 F S 0 CH₃ CF₃ H —CH₃ 2-894 F S 0 CH₃ CF₃ H — C₂H₅ 2-895 F S 0 CH₃ CF₃ H — ^(n)C₃H₇ 2-896F S 0 CH₃ CF₃ H — ^(n)C₄H₉ 2-897 F S 0 CH₃ CF₃ H — ^(i)C₃H₇ 2-898 F S 0CH₃ CF₃ H — ^(s)C₄H₉ 2-899 F S 0 CH₃ CF₃ H — CH₂CH₂Cl 2-900 F S 0 CH₃CF₃ H — CH₂CH₂Br 2-901 F S 0 CH₃ CF₃ H — CH₂CH═CH₂ 2-902 F S 0 CH₃ CF₃ H— CH(CH₃)CH═CH₂ 2-903 F S 0 CH₃ CF₃ H — CH₂CCl═CH₂ 2-904 F S 0 CH₃ CF₃ H— CH₂C≡CH 2-905 F S 0 CH₃ CF₃ H — CH(CH₃)C≡CH 2-906 F S 0 CH₃ CF₃ H —CH₂CN 2-907 F S 0 CH₃ CF₃ H — CH₂OCH₃ 2-908 F S 0 CH₃ CF₃ H — CH₂OC₂H₅2-909 F S 0 CH₃ CF₃ H — CH₂COOH 2-910 F S 0 CH₃ CF₃ H — CH₂COOCH₃ 2-911F S 0 CH₃ CF₃ H — CH₂COOC₂ ⁻H₅ 2-912 F S 0 CH₃ CF₃ H — CH₂COO^(n)C₃H₇2-913 F S 0 CH₃ CF₃ H — CH₂COO^(n)C₄H₉ 2-914 F S 0 CH₃ CF₃ H —CH₂COO^(n)C₅H₁₁ 2-915 F S 0 CH₃ CF₃ H — CH₂COO^(i)C₃H₇ 2-916 F S 0 CH₃CF₃ H — CH₂COO^(c)C₅H₉ 2-917 F S 0 CH₃ CF₃ H — CH₂COO^(c)C₆H₁₁ 2-918 F S0 CH₃ CF₃ H — CH(CH₃)COOH 2-919 F S 0 CH₃ CF₃ H — CH(CH₃)COOCH₃ 2-920 FS 0 CH₃ CF₃ H — CH(GH3 )COOC₂H₅ 2-921 F S 0 CH₃ CF₃ H —CH(CH₃)COO^(n)C₃H₇ 2-922 F S 0 CH₃ CF₃ H — CH(CH₃)COO^(n)C₄H₉ 2-923 F S0 CH₃ CF₃ H — CH(CH₃)COO^(n)C₅H₁₁ 2-924 F S 0 CH₃ CF₃ H —CH(CH₃)COO^(i)C₃H₇ 2-925 F S 0 CH₃ CF₃ H — CH(CH₃)COO^(c)C₆H₉ 2-926 F S0 CH₃ CF₃ H — CH(CH₃)COO^(c)C₆H₁₁ 2-927 H O 0 CH₃ CF₃ H — H 2-928 H O 0CH₃ CF₃ H — CH₃ 2-929 H O 0 CH₃ CF₃ H — C₂H₅ 2-930 H O 0 CH₃ CF₃ H —^(n)C₃H₇ 2-931 H O 0 CH₃ CF₃ H — ^(n)C₄H₉ 2-932 H O 0 CH₃ CF₃ H —^(i)C₃H₇ 2-933 H O 0 CH₃ CF₃ H — ^(i)C₄H₉ 2-934 H O 0 CH₃ CF₃ H —CH₂CH═³¹ CH₂ 2-935 H O 0 CH₃ CF₃ H — CH(CH₃)CH═CH₂ 2-936 H O 0 CH₃ CF₃ H— CH₂C≡CH 2-937 H O 0 CH₃ CF₃ H — CH(CH₃)C≡CH 2-938 H O 0 CH₃ CF₃ H —CH₂OCH₃ 2-939 H O 0 CH₃ CF₃ H — CH₂OC₂H₅ 2-940 F O 0 CH₃ CF₃ H — H 2-941F O 0 CH₃ CF₃ H — CH₃ 2-942 F O 0 CH₃ CF₃ H — C₂H₅ 2-943 F O 0 CH₃ CF₃ H— ^(n)C₃H₇ 2-944 F O 0 CH₃ CF₃ H — ^(n)C₄H₉ 2-945 F O 0 CH₃ CF₃ H —CH₂CH═CH₂ 2-946 F 0 0 CH₃ CF₃ H — CH(CH₃)CH═CH₂ 2-947 F O 0 CH₃ CF₃ H —CH₂C≡CH 2-948 F O 0 CH₃ CF₃ H — CH(CH₃)C≡CH 2-949 F O 0 CH₃ CF₃ H —CH₂OCH₃ 2-950 F O 0 CH₃ CF₃ H — CH₂OC₂H₅

[0806] TABLE 3 Compounds of the formula:

Compound No. X Y Z² R³ R¹ R² R⁶ 3-1 H F O H CF₂Cl H CH₃ 3-2 H Cl O HCF₂Cl H CH₃ 3-3 H Br O H CF₂Cl H CH₃ 3-4 F F O H CF₂Cl H CH₃ 3-5 F Cl OH CF₂Cl H CH₃ 3-6 F Br O H CF₂Cl H CH₃ 3-7 H F O H CF₂Cl CH₃ CH₃ 3-8 HCl O H CF₂Cl CH₃ CH₃ 3-9 H Br O H CF₂Cl CH₃ CH₃ 3-10 F F O H CF₂Cl CH₃CH₃ 3-11 F Cl O H CF₂Cl CH₃ CH₃ 3-12 F Br O H CF₂Cl CH₃ CH₃ 3-13 H F O HCF₂Cl H C₂H₆ 3-14 H Cl O H CF₂Cl H C₂H₅ 3-15 H Br O H CF₂Cl H C₂H₅ 3-16F F O H CF₂Cl H C₂H₅ 3-17 F Cl O H CF₂Cl H C₂H₅ 3-18 F Br O H CF₂Cl HC₂H₅ 3-19 H F O H CF₂Cl CH C₂H₅ 3-20 H Cl O H CF₂Cl CH₃ C₂H₅ 3-21 H Br OH CF₂Cl CH₃ C₂H₅ 3-22 F F O H CF₂Cl CH₃ C₂H₅ 3-23 F Cl O H CF₂Cl CH₃C₂H₅ 3-24 F Br O H CF₂Cl CH₃ C₂H₅ 3-25 H F O H CF₂Cl CH₃ CH₂Br 3-26 H FO H CF₂Cl CH₃ CHBr₂ 3-27 H F O H CF₂Cl CH₃ CBr₃ 3-28 H F O H CF₂Cl CH₃CHO 3-29 H F O H CF₂Cl CH₃ CN 3-30 H F O H CF₂Cl CH₃ COOH 3-31 H F O HCF₂Cl CH₃ CH₂OH 3-32 H F O H CF₂Cl CH₃ CH₂OCH₃ 3-33 H F O H CF₂Cl CH₃CH₂OC₂H₅ 3-34 H F O H CF₂Cl CH₃ CH₂O^(i)C₃H₇ 3-35 H F O H CF₂Cl CH₃CH₂OCH₂OCH₃ 3-36 H F O H CF₂Cl CH₃ CH₂OCH₂OC₂H₅ 3-37 H F O H CF₂Cl CH₂CH₂OCOCH₃ 3-38 H F O H CF₂Cl CH₃ CH₂OCOC₂H₅ 3-39 H F O H CF₂Cl CH₃CH₂OCO^(i)C₃H₇ 3-40 H F O H CF₂Cl CH₃ CH₂OCOCH₂Cl 3-41 H F O H CF₂Cl CH₃CH₂OCOCCl₃ 3-42 H F O H CF₂Cl CH₃ CH₂OCOCF₃ 3-43 H F O H CF₂Cl CH₃COOCH₃ 3-44 H F O H CF₂Cl CH₃ COOC₂H₅ 3-45 H F O H CF₂Cl CH₃ COO^(n)C₃H₇3-46 H F O H CF₂Cl CH₃ COO^(n)C₃H₉ 3-47 H F O H CF₂Cl CH₃ COO^(n)C₅H₁₁3-48 H F O H CF₂Cl CH₃ COO^(i)C₃H₇ 3-49 H F O H CF₂Cl CH₃ COCH₃ 3-50 H FO H CF₂Cl CH₃ COC₂H₅ 3-51 H Cl O H CF₂Cl CH₃ CH₂Br 3-52 H Cl O H CF₂ClCH₃ CHBr₂ 3-53 H Cl O H CF₂Cl CH₃ CBr₃ 3-54 H Cl O H CF₂Cl CH₃ CHO 3-55H Cl O H CF₂Cl CH₃ CN 3-56 H Cl O H CF₂Cl CH₃ COOH 3-57 H Cl O H CF₂ClCH₃ CH₂CH 3-58 H Cl O H CF₂Cl CH₃ CH₂OCH₃ 3-59 H Cl O H CF₂Cl CH₃CH₂OC₂H₆ 3-60 H Cl O H CF₂Cl CH₃ CH₂O^(i)C₃H₇ 3-61 H Cl O H CF₂Cl CH₃CH₂OCH₂OCH₃ 3-62 H Cl O H CF₂Cl CH₃ CH₂OCH₂OC₂H₅ 3-63 H Cl O H CF₂Cl CH₃CH₂OCOCH₃ 3-64 H Cl O H CF₂Cl CH₃ CH₂OCOC₂H₅ 3-65 H Cl O H CF₂Cl CH₃CH₂OCO^(i)C₃H₇ 3-66 H Cl O H CF₂Cl CH₃ CH₂OCOCH₂Cl 3-67 H Cl O H CF₂ClCH₃ CH₂OCOCCl₃ 3-67 H Cl O H CF₂Cl CH₃ CH₂OCOCF₃ 3-69 H Cl O H CF₂Cl CH₃COOCH₃ 3-70 H Cl O H CF₂Cl CH₃ COOC₂H₅ 3-71 H Cl O H CF₂Cl CH₃COO^(n)C₃H₇ 3-72 H Cl O H CF₂Cl CH₃ COO^(n)C₄H₉ 3-73 H Cl O H CF₂Cl CH₃COO^(n)C₅H₁₁ 3-74 H Cl O H CF₂Cl CH₃ COO^(i)C₃H₇ 3-75 H Cl O H CF₂Cl CH₃COCH₃ 3-76 H Cl O H CF₂Cl CH₃ COC₂H₃ 3-77 F F O H CF₂Cl CH₃ CH₂Br 3-78 FF O H CF₂Cl CH₃ CHBr₂ 3-79 F F O H CF₂Cl CH₃ CBr₃ 3-80 F F O H CF₂Cl CH₃CHO 3-81 F F O H CF₂Cl CH₃ CN 3-82 F F O H CF₂Cl CH₃ COOH 3-83 F F O HCF₂Cl CH₃ CH₂OH 3-84 F F O H CF₂Cl CH₃ CH₂OCH₃ 3-85 F F O H CF₂Cl CH₃CH₂OC₂H₅ 3-86 F F O H CF₂Cl CH₃ CH₂O^(i)C₃H₇ 3-87 F F O H CF₂Cl CH₃CH₂OCH₂OCH₃ 3-88 F F O H CF₂Cl CH₃ CH₂OCH₂OC₂H₅ 3-89 F F O H CF₂Cl CH₃CH₂OCOCH₃ 3-90 F F O H CF₂Cl CH₃ CH₂OCOC₂H₅ 3-91 F F O H CF₂Cl CH₃CH₂OCO^(i)C₃H₇ 3-92 F F O H CF₂Cl CH₃ CH₂OCOCH₂Cl 3-93 F F O H CF₂Cl CH₃CH₂OCOCCl₃ 3-94 F F O H CF₂Cl CH₃ CH₂OCOCF₃ 3-95 F F O H CF₂Cl CH₃COOCH₃ 3-96 F F O H CF₂Cl CH₃ COOC₂H₅ 3-97 F F O H CF₂Cl CH₃ COO^(n)C₃H₇3-98 F F O H CF₂Cl CH₃ COO^(n)C₄H₉ 3-99 F F O H CF₂Cl CH₃ COO^(n)C₅H₁₁3-100 F F O H CF₂Cl CH₃ COO^(i)C₃H₇ 3-101 F F O H CF₂Cl CH₃ COCH₃ 3-102F F O H CF₂Cl CH₂ COC₂H₅ 3-103 F Cl O H CF₂Cl CH₃ CH₂Br 3-104 F Cl O HCF₂Cl CH₃ CHBr₂ 3-105 F Cl O H CF₂Cl CH₃ CBr₃ 3-106 F Cl O H CF₂Cl CH₃CHO 3-107 F Cl O H CF₂Cl CH₃ CN 3-108 F Cl O H CF₂Cl CH₃ COOH 3-109 F ClO H CF₂Cl CH₃ CH₂OH 3-110 F Cl O H CF₂Cl CH₃ CH₂OCH₃ 3-111 F Cl O HCF₂Cl CH₃ CH₂OC₂H₅ 3-112 F Cl O H CF₂Cl CH₃ CH₂O^(i)C₃H₇ 3-113 F Cl O HCF₂Cl CH₃ CH₂OCH₂OCH₃ 3-114 F Cl O H CF₂Cl CH₃ CH₂OCH₂OC₂H₅ 3-115 F Cl OH CF₂Cl CH₃ CH₂OCOCH₃ 3-116 F Cl O H CF₂Cl CH₃ CH₂OCOC₂H₅ 3-117 F Cl O HCF₂Cl CH₃ CH₂OCO^(i)C₃H₇ 3-118 F Cl O H CF₂Cl CH₃ CH₂OCOCH₂Cl 3-119 F ClO H CF₂Cl CH₃ CH₂OCOCCl₃ 3-120 F Cl O H CF₂Cl CH₃ CH₂OCOCF₃ 3-121 F Cl OH CF₂Cl CH₃ COOCH₃ 3-122 F Cl O H CF₂Cl CH₃ COOC₂H₅ 3-123 F Cl O H CF₂ClCH₃ COO^(n)C₃H₇ 3-124 F Cl O H CF₂Cl CH₃ COO^(n)C₄H₉ 3-125 F Cl O HCF₂Cl CH₃ COO^(n)C₅H₁₁ 3-126 F Cl O H CF₂Cl CH₃ COO^(i)C₃H₇ 3-127 F Cl OH CF₂Cl CH₃ COCH₃ 3-128 F Cl O H CF₂Cl CH₃ COC₂H₅ 3-129 H F O H CF₃ HCH₃ 3-130 H Cl O H CF₃ H CH₃ 3-131 H Br O H CF₃ H CH₃ 3-132 F F O H CF₃H CH₃ 3-133 F Cl O H CF₃ H CH₃ 3-134 F Br O H CF₃ H CH₃ 3-135 H F O HCF₃ CH₃ CH₃ 3-136 H Cl O H CF₃ CH₃ CH₃ 3-137 H Br O H CF₃ CH₃ CH₃ 3-138F F O H CF₃ CH₃ CH₃ 3-139 F Cl O H CF₃ CH₃ CH₃ 3-140 F Br O H CF₃ CH₃CH₃ 3-141 H F O H CF₃ H C₂H₅ 3-142 H Cl O H CF₃ H C₂H₅ 3-143 H Br O HCF₃ H C₂H₅ 3-144 F F O H CF₃ H C₂H₅ 3-145 F Cl O H CF₃ H C₂H₅ 3-146 F BrO H CF₃ H C₂H₅ 3-147 H F O H CF₃ CH₃ C₂H₅ 3-148 H Cl O H CF₃ CH₃ C₂H₅3-149 H Br O H CF₃ CH₃ C₂H₅ 3-150 F F O H CF₃ CH₃ C₂H₅ 3-151 F Cl O HCF₃ CH₃ C₂H₅ 3-152 F Br O H CF₃ CH₃ C₂H₅ 3-153 H F O H CF₃ CH₃ CH₂Br3-154 H F O H CF₃ CH₃ CHBr₂ 3-155 H F O H CF₃ CH₃ CBr₃ 3-156 H F O H CF₃CH₃ CHO 3-157 H F O H CF₃ CH₃ CN 3-158 H F O H CF₃ CH₃ COOH 3-159 H F OH CF₃ CH₃ CH₂OH 3-160 H F O H CF₃ CH₃ CH₂OC₃ 3-161 H F O H CF₃ CH₃CH₂OC₂H₅ 3-162 H F O H CF₃ CH₃ CH₂O^(i)C₃H₇ 3-163 H F O H CF₃ CH₃CH₂OCH₂OCH₃ 3-164 H F O H CF₃ CH₃ CH₂OCH₂OC₂H₅ 3-165 H F O H CF₃ CH₃CH₂OCOCH₃ 3-166 H F O H CF₃ CH₃ CH₂OCOC₂H₅ 3-167 H F O H CF₃ CH₃CH₂OCO^(i)C₃H₇ 3-168 H F O H CF₃ CH₃ CH₂OCOCH₂Cl 3-169 H F O H CF₃ CH₃CH₂OCOCCl₃ 3-170 H F O H CF₃ CH₃ CH₂OCOCF₃ 3-171 H F O H CF₃ CH₃ COOCH₃3-172 H F O H CF₃ CH₃ COOC₂H₆ 3-173 H F O H CF₃ CH₃ COO^(n)C₃H₇ 3-174 HF O H CF₃ CH₃ COO^(n)C⁴H⁹ 3-175 H F O H CF₃ CH₃ COO^(n)C₅H₁₁ 3-176 H F OH CF₃ CH₃ COO^(i)C₃H₇ 3-177 H F O H CF₃ CH₃ COCH₃ 3-178 H F O H CF₃ CH₃COC₂H₅ 3-179 H Cl O H CF₃ CH₃ CH₂Br 3-180 H Cl O H CF₃ CH₃ CHBr₂ 3-181 HCl O H CF₃ CH₃ CBr₃ 3-182 H Cl O H CF₃ CH₃ CHO 3-183 H Cl O H CF₃ CH₃ CN3-184 H Cl O H CF₃ CH₃ COOH 3-185 H Cl O H CF₃ CH₃ CH₂OH 3-186 H Cl O HCF₃ CH₃ CH₂OCH₃ 3-187 H Cl O H CF₃ CH₃ CH₂OC₂H₅ 3-188 H Cl O H CF₃ CH₃CH₂O^(i)C₃H₇ 3-189 H Cl O H CF₃ CH₃ CH₂OCH₂OCH₃ 3-190 H Cl O H CF₃ CH₃CH₂OCH₂OC₂H₅ 3-191 H Cl O H CF₃ CH₃ CH₂OCOCH₃ 3-192 H Cl O H CF₃ CH₃CH₂OCOC₂H₅ 3-193 H Cl O H CF₃ CH₃ CH₂OCO^(i)C₃H₇ 3-194 H Cl O H CF₃ CH₃CH₂OCOCH₂Cl 3-195 H Cl O H CF₃ CH₃ CH₂OCOCCl₃ 3-196 H Cl O H CF₃ CH₃CH₂OCOCF₃ 3-197 H Cl O H CF₃ CH₃ COOCH₃ 3-198 H Cl O H CF₃ CH₃ COOC₂H₅3-199 H Cl O H CF₃ CH₃ COO^(n)C₃H₇ 3-200 H Cl O H CF₃ CH₃ COO^(n)C₄H₉3-201 H Cl O H CF₃ CH₃ COO^(n)C₅H₁₁ 3-202 H Cl O H CF₃ CH₃ COO^(i)C₃H₇3-203 H Cl O H CF₃ CH₃ COCH₃ 3-204 H Cl O H CF₃ CH₃ COC₂H₅ 3-205 F F O HCF₃ CH₃ CH₂Br 3-206 F F O H CF₃ CH₃ CHBr₂ 3-207 F F O H CF₃ CH₃ CBr₃3-208 F F O H CF₃ CH₃ CHO 3-209 F F O H CF₃ CH₃ CN 3-210 F F O H CF₃ CH₃COOH 3-211 F F O H CF₃ CH₃ CH₂OH 3-212 F F O H CF₃ CH₃ CH₂OCH₃ 3-213 F FO H CF₃ CH₃ CH₂OC₂H₅ 3-214 F F O H CF₃ CH₃ CH₂O^(i)C₃H₇ 3-215 F F O HCF₃ CH₃ CH₂OCH₂OCH₃ 3-216 F F O H CF₃ CH₃ CH₂OCH₂OC₂H₅ 3-217 F F O H CF₃CH₃ CH₂OCOCH₃ 3-218 F F O H CF₃ CH₃ CH₂OCOC₂H₅ 3-219 F F O H CF₃ CH₃CH₂OCO^(i)C₃H₇ 3-220 F F O H CF₃ CH₃ CH₂OCOCH₂Cl 3-221 F F O H CF₃ CH₃CH₂OCOCCl₃ 3-222 F F O H CF₃ CH₃ CH₂OCOCF₃ 3-223 F F O H CF₃ CH₃ COOCH₃3-224 F F O H CF₃ CH₃ COOC₂H₅ 3-225 F F O H CF₃ CH₃ COO^(n)C₃H₇ 3-226 FF O H CF₃ CH₃ COO^(n)C₄H₉ 3-227 F F O H CF₃ CH₃ COO^(n) C₅H₁₁ 3-228 F FO H CF₃ CH₃ COO^(i)C₃H₇ 3-229 F F O H CF₃ CH₃ COCH₃ 3-230 F F O H CF₃CH₃ COC₂H₅ 3-231 F Cl O H CF₃ CH₃ CH₂Br 3-232 F Cl O H CF₃ CH₃ CHBr₂3-233 F Cl O H CF₃ CH₃ CBr₃ 3-234 F Cl O H CF₃ CH₃ CHO 3-235 F Cl O HCF₃ CH₃ CN 3-236 F Cl O H CF₃ CH₃ COOH 3-237 F Cl O H CF₃ CH₃ CH₂OH3-238 F Cl O H CF₃ CH₃ CH₂OCH₃ 3-239 F Cl O H CF₃ CH₃ CH₂OC₂H₅ 3-240 FCl O H CF₃ CH₃ CH₂I^(i)C₃H₇ 3-241 F Cl O H CF₃ CH₃ CH₂OCH₂OCH₃ 3-242 FCl O H CF₃ CH₃ CH₂OCH₂OC₂H₅ 3-243 F Cl O H CF₃ CH₃ CH₂OCOCH₃ 3-244 F ClO H CF₃ CH₃ CH₂OCOC₂H₅ 3-245 F Cl O H CF₃ CH₃ CH₂OCO^(i)C₃H₇ 3-246 F ClO H CF₃ CH₃ CH₂OCOCH₂Cl 3-247 F Cl O H CF₃ CH₃ CH₂OCOCCl₃ 3-248 F Cl O HCF₃ CH₃ CH₂OCOCF₃ 3-249 F Cl O H CF₃ CH₃ COOCH₃ 3-250 F Cl O H CF₃ CH₃COOC₂H₅ 3-251 F Cl O H CF₃ CH₃ COO^(n)C₃H₇ 3-252 F Cl O H CF₃ CH₃COO^(n)C₄H₉ 3-253 F Cl O H CF₃ CH₃ COO^(n)C₅H₁₁ 3-254 F Cl O H CF₃ CH₃COO^(i)C₃H₇ 3-255 F Cl O H CF₃ CH₃ COCH₃ 3-256 F Cl O H CF₃ CH₃ COC₂H₅3-257 H F O H CF₂Cl H CH₂Br 3-258 H F O H CF₂Cl H CHBr₂ 3-259 H F O HCF₂Cl H CBr₃ 3-260 H F O H CF₂Cl H CHO 3-261 H F O H CF₂Cl H CN 3-262 HF O H CF₂Cl H COOH 3-263 H F O H CF_(2 Cl) H CH₂OH 3-264 H F O H CF₂Cl HCH₂OCH₃ 3-265 H F O H CF₂Cl H CH₂OC₂H₅ 3-266 H F O H CF₂Cl HCH₂O^(i)C₃H₇ 3-267 H F O H CF₂Cl H CH₂OCH₂OCH₃ 3-268 H F O H CF₂Cl HCH₂OCH₂OC₂H₅ 3-269 H F O H CF₂Cl H CH₂OCOCH₃ 3-270 H F O H CF₂Cl HCH₂OCOC₂H₅ 3-271 H F O H CF₂Cl H CH₂OCO^(i)C₃H₇ 3-272 H F O H CF₂Cl HCH₂OCOCH₂Cl 3-273 H F O H CF₂Cl H CH₂OCOCCl₃ 3-274 H F O H CF₂Cl HCH₂OCOCF₃ 3-275 H F O H CF₂Cl H COOCH₃ 3-276 H F O H CF₂Cl H COOC₂H₅3-277 H F O H CF₂Cl H COO^(n)C₃H₇ 3-278 H F O H CF₂Cl H COO^(n)C₄H₉3-279 H F O H CF₂Cl H COO^(n)C₅H₁₁ 3-280 H F O H CF₂Cl H COO^(i)C₃H₇3-281 H F O H CF₂Cl H COCH₃ 3-282 H F O H CF₂Cl H COC₂H₅ 3-283 H Cl O HCF₂Cl H CH₂Br 3-284 H Cl O H CF₂Cl H CHBr₂ 3-285 H Cl O H CF₂Cl H CBr₃3-286 H Cl O H CF₂Cl H CHO 3-287 H Cl O H CF₂Cl H CN 3-288 H Cl O HCF₂Cl H COOH 3-289 H Cl O H CF₂Cl H CH₂OH 3-290 H Cl O H CF₂Cl H CH₂OCH₃3-291 H Cl O H CF₂Cl H CH₂OC₂H₅ 3-292 H Cl O H CF₂Cl H CH₂O^(i)C₃H₇3-293 H Cl O H CF₂Cl H CH₂OCH₂OCH₃ 3-294 H Cl O H CF₂Cl H CH₂OCH₂OC₂H₅3-295 H Cl O H CF₂Cl H CH₂OCOCH₃ 3-296 H Cl O H CF₂Cl H CH₂OCOC₂H₅ 3-297H Cl O H CF₂Cl H CH₂OCO^(i)C₃H₇ 3-298 H Cl O H CF_(2 Cl) H CH₂OCOCH₂Cl3-299 H Cl O H CF₂Cl H CH₂OCOCCl₃ 3-300 H Cl O H CF₂Cl H CH₂OCOCF₃ 3-301H Cl O H CF₂Cl H COOCH₃ 3-302 H Cl O H CF₂Cl H COOC₂H₅ 3-303 H Cl O HCF₂Cl H COO^(n)C₃H₇ 3-304 H Cl O H CF₂Cl H COO^(n)C₄H₉ 3-305 H Cl O HCF₂Cl H COO^(n)C₅H₁₁ 3-306 H Cl O H CF₂Cl H COO^(i)C₃H₇ 3-307 H Cl O HCF₂Cl H COCH₃ 3-308 H Cl O H CF₂Cl H COC₂H₅ 3-309 F F O H CF₂Cl H CH₂Br3-310 F F O H CF₂Cl H CHBr₂ 3-311 F F O H CF₂Cl H CBr₃ 3-312 F F O HCF₂Cl H CHO 3-313 F F O H CF₂Cl H CN 3-314 F F O H CF₂Cl H COOH 3-315 FF O H CF₂Cl H CH₂OH 3-316 F F O H CF₂Cl H CH₂OCH₃ 3-317 F F O H CF₂Cl HCH₂OC₂H₅ 3-318 F F O H CF₂Cl H CH₂O^(i)C₃H₇ 3-319 F F O H CF₂Cl HCH₂OCH₂OCH₃ 3-320 F F O H CF₂Cl H CH₂OCH₂OC₂H₅ 3-321 F F O H CF₂Cl HCH₂OCOCH₃ 3-322 F F O H CF₂Cl H CH₂OCOC₂H₅ 3-323 F F O H CF₂Cl HCH₂OCO^(i)C₃H₇ 3-324 F F O H CF₂Cl H CH₂OCOCH₂Cl 3-325 F F O H CF₂Cl HCH₂OCOCCl₃ 3-326 F F O H CF₂Cl H CH₂OCOCF₃ 3-327 F F O H CF₂Cl H COOCH₃3-328 F F O H CF₂Cl H COOC₂H₅ 3-329 F F O H CF₂Cl H COO^(n)C₃H₇ 3-330 FF O H CF_(2 Cl) H COO^(n)C₄H₉ 3-331 F F O H CF_(2 Cl) H COO^(n)C₅H₁₁3-332 F F O H CF₂Cl H COO^(i)C₃H₇ 3-333 F F O H CF₂Cl H COCH₃ 3-334 F FO H CF₂Cl H COC₂H₅ 3-335 F Cl O H CF₂Cl H CH₂Br 3-336 F Cl O H CF₂Cl HCHBr₂ 3-337 F Cl O H CF₂Cl H CBr₃ 3-338 F Cl O H CF₂Cl H CHO 3-339 F ClO H CF₂Cl H CN 3-340 F Cl O H CF₂Cl H COCH 3-341 F Cl O H CF₂Cl H CH₂OH3-342 F Cl O H CF₂Cl H CH₂OCH₃ 3-343 F Cl O H CF₂Cl H CH₂OC₂H₅ 3-344 FCl O H CF₂Cl H CH₂O^(i)C₃H₇ 3-345 F Cl O H CF₂Cl H CH₂OCH₂OCH₃ 3-346 FCl O H CF₂Cl H CH₂OCH₂OC₂H₅ 3-347 F Cl O H CF₂Cl H CH₂OCOCH₃ 3-348 F ClO H CF₂Cl H CH₂OCOC₂H₅ 3-349 F Cl O H CF₂Cl H CH₂OCO^(i)C₃H₇ 3-350 F ClO H CF₂Cl H CH₂OCOCH₂Cl 3-351 F Cl O H CF₂Cl H CH₂OCOCCl₃ 3-352 F Cl O HCF₂Cl H CH₂OCOCF₃ 3-353 F Cl O H CF₂Cl H COOCH₃ 3-354 F Cl O H CF₂Cl HCOOC₂H₅ 3-355 F Cl O H CF₂Cl H COO^(n)C₃H₇ 3-356 F Cl O H CF₂Cl HCOO^(n)C₄H₉ 3-357 F Cl O H CF₂Cl H COO^(n)C₅H₁₁ 3-358 F Cl O H CF₂Cl HCOO^(i)C₃H₇ 3-359 F Cl O H CF₂Cl H COCH₃ 3-360 F Cl O H CF₂Cl H COC₂H₅3-361 F Br O H CF₃ H C₂H₅ 3-362 H F O H CF₃ H CH₂Br 3-363 H F O H CF₃ HCHBr₂ 3-364 H F O H CF₃ H CBr₃ 3-365 H F O H CF₃ H CHO 3-366 H F O H CF₃H CN 3-367 H F O H CF₃ H COOH 3-368 H F O H CF₃ H CH₂OH 3-369 H F O HCF₃ H CH₂OCH₃ 3-370 H F O H CF₃ H CH₂OC₂H₅ 3-371 H F O H CF₃ HCH₂O^(i)C₃H₇ 3-372 H F O H CF₃ H CH₂OCH₂OCH₃ 3-373 H F O H CF₃ HCH₂OCH₂OC₂H₅ 3-374 H F O H CF₃ H CH₂OCOCH₃ 3-375 H F O H CF₃ HCH₂OCOC₂H₅ 3-376 H F O H CF₃ H CH₂OCO^(i)C₃H₇ 3-377 H F O H CF₃ HCH₂OCOCH₂Cl 3-378 H F O H CF₃ H CH₂OCOCCl₃ 3-379 H F O H CF₃ H CH₂OCOCF₃3-380 H F O H CF₃ H COOCH₃ 3-381 H F O H CF₃ H COOC₂H₅ 3-382 H F O H CF₃H COO^(n)C₃H₇ 3-383 H F O H CF₃ H COO^(n)C₄H₉ 3-384 H F O H CF₃ HCOO^(n)C₅H₁₁ 3-385 H F O H CF₃ H COO^(i)C₃H₇ 3-386 H F O H CF₃ H COCH₃3-387 H F O H CF₃ H COC₂H₅ 3-388 H Cl O H CF₃ H CH₂Br 3-389 H Cl O H CF₃H CHBr₂ 3-390 H Cl O H CF₃ H CBr₃ 3-391 H Cl O H CF₃ H CHO 3-392 H Cl OH CF₃ H CN 3-393 H Cl O H CF₃ H COOH 3-394 H Cl O H CF₃ H CH₂OH 3-395 HCl O H CF₃ H CH₂OCH₃ 3-396 H Cl O H CF₃ H CH₂OC₂H₅ 3-397 H Cl O H CF₃ HCH₂O^(i)C₃H₇ 3-398 H Cl O H CF₃ H CH₂OCH₂OCH₃ 3-399 H Cl O H CF₃ HCH₂OCH₂OC₂H₅ 3-400 H Cl O H CF₃ H CH₂OCOCH₃ 3-401 H Cl O H CF₃ HCH₂OCOC₂H₆ 3-402 H Cl O H CF₃ H CH₂OCO^(i)C₃H₇ 3-403 H Cl O H CF₃ HCH₂OCOCH₂Cl 3-404 H Cl O H CF₃ H CH₂OCOCCl₃ 3-405 H Cl O H CF₃ HCH₂OCOCF₃ 3-406 H Cl O H CF₃ H COOCH₃ 3-407 H Cl O H CF₃ H COOC₂H₅ 3-408H Cl O H CF₃ H COO^(n)C₃H₇ 3-409 H Cl O H CF₃ H COO^(n)C₄H₉ 3-410 H Cl OH CF₃ H COO^(n)C₅H₁₁ 3-411 H Cl O H CF₃ H COO^(i)C₃H₇ 3-412 H Cl O H CF₃H COCH₃ 3-413 H Cl O H CF₃ H COC₂H₅ 3-414 F F O H CF₃ H CH₂Br 3-415 F FO H CF₃ H CHBr₂ 3-416 F F O H CF₃ H CBr₃ 3-417 F F O H CF₃ H CHO 3-418 FF O H CF₃ H CN 3-419 F F O H CF₃ H COOH 3-420 F F O H CF₃ H CH₂OH 3-421F F O H CF₃ H CH₂OCH₃ 3-422 F F O H CF₃ H CH₂OC₂H₅ 3-423 F F O H CF₃ HCH₂O^(i)C₃H₇ 3-424 F F O H CF₃ H CH₂OCH₂OCH₃ 3-425 F F O H CF₃ HCH₂OCH₂OC₂H₅ 3-426 F F O H CF₃ H CH₂OCOCH₃ 3-427 F F O H CF₃ HCH₂OCOC₂H₅ 3-428 F F O H CF₃ H CH₂OCO^(i)C₃H₇ 3-429 F F O H CF₃ HCH₂OCOCH₂Cl 3-430 F F O H CF₃ H CH₂OCOCCl₃ 3-431 F F O H CF₃ H CH₂OCOCF₃3-432 F F O H CF₃ H COOCH₃ 3-433 F F O H CF₃ H COOC₂H₅ 3-434 F F O H CF₃H COO^(n)C₃H₇ 3-435 F F O H CF₃ H COO^(n)C₄H₉ 3-436 F F O H CF₃ HCOO^(n)C₅H₁₁ 3-437 F F O H CF₃ H COO^(i)C₃H₇ 3-438 F F O H CF₃ H COCH₃3-439 F F O H CF₃ H COC₂H₅ 3-440 F Cl O H CF₃ H CH₂Br 3-441 F Cl O H CF₃H CHBr₂ 3-442 F Cl O H CF₃ H CBr₃ 3-443 F Cl O H CF₃ H CHO 3-444 F Cl OH CF₃ H CN 3-445 F Cl O H CF₃ H COOH 3-446 F Cl O H CF₃ H CH₂OH 3-447 FCl O H CF₃ H CH₂OCH₃ 3-448 F Cl O H CF₃ H CH₂OC₂H₅ 3-449 F Cl O H CF₃ HCH₂O^(i)C₃H₇ 3-450 F Cl O H CF₃ H CH₂OCH₂OCH₃ 3-451 F Cl O H CF₃ HCH₂OCH₂OC₂H₅ 3-452 F Cl O H CF₃ H CH₂OCOCH₃ 3-453 F Cl O H CF₃ HCH₂OCOC₂H₅ 3-454 F Cl O H CF₃ H CH₂OCO^(i)C₃H₇ 3-455 F Cl O H CF₃ HCH₂OCOCH₂Cl 3-456 F Cl O H CF₃ H CH₂OCOCCl₃ 3-457 F Cl O H CF₃ HCH₂OCOCF₃ 3-458 F Cl O H CF₃ H COOCH₃ 3-459 F Cl O H CF₃ H COOC₂H₅ 3-460F Cl O H CF₃ H COO^(n)C₃H₇ 3-461 F Cl O H CF₃ H COO^(n)C₄H₉ 3-462 F Cl OH CF₃ H COO^(n)C₅H₁₁ 3-463 F Cl O H CF₃ H COO^(i)C₃H₇ 3-464 F Cl O H CF₃H COCH₃ 3-465 F Cl O H CF₃ H COC₂H₅ 3-466 H F O CH₃ CF₃ H CH₃ 3-467 H ClO CH₃ CF₃ H CH₃ 3-468 H Br O CH₃ CF₃ H CH₃ 3-469 F F O CH₃ CF₃ H CH₃3-470 F Cl O CH₃ CF₃ H CH₃ 3-471 F Br O CH₃ CF₃ H CH₃ 3-472 H F O CH₃CF₃ H C₂H₅ 3-473 H Cl O CH₃ CF₃ H C₂H₅ 3-474 H Br O CH₃ CF₃ H C₂H₅ 3-475F F O CH₃ CF₃ H C₂H₅ 3-476 F Cl O CH₃ CF₃ H C₂H₅ 3-477 F Br O CH₃ CF₃ HC₂H₅ 3-478 F Br O CH₃ CF₃ H C₂H₅ 3-479 H F O CH₃ CF₃ H CH₂Br 3-480 H F OCH₃ CF₃ H CHBr₂ 3-481 H F O CH₃ CF₃ H CBr₃ 3-482 H F O CH₃ CF₃ H CHO3-483 H F O CH₃ CF₃ H CN 3-484 H F O CH₃ CF₃ H COOH 3-485 H F O CH₃ CF₃H CH₂OH 3-486 H F O CH₃ CF₃ H CH₂OCH₃ 3-487 H F O CH₃ CF₃ H CH₂OC₂H₅3-488 H F O CH₃ CF₃ H CH₂O^(i)C₃H₇ 3-489 H F O CH₃ CF₃ H CH₂OCH₂OCH₃3-490 H F O CH₃ CF₃ H CH₂OCH₂OC₂H₅ 3-491 H F O CH₃ CF₃ H CH₂OCOCH₃ 3-492H F O CH₃ CF₃ H CH₂OCOC₂H₅ 3-493 H F O CH₃ CF₃ H CH₂OCO^(i)C₃H₇ 3-494 HF O CH₃ CF₃ H CH₂OCOCH₂Cl 3-495 H F O CH₃ CF₃ H CH₂OCOCCl₃ 3-496 H F OCH₃ CF₃ H CH₂OCOCF₃ 3-497 H F O CH₃ CF₃ H COOCH₃ 3-498 H F O CH₃ CF₃ HCOOC₂H₅ 3-499 H F O CH₃ CF₃ H COO^(n)C₃H₇ 3-500 H F O CH₃ CF₃ HCOO^(n)C₄H₉ 3-501 H F O CH₃ CF₃ H COO^(n)C₅H₁₁ 3-502 H F O CH₃ CF₃ HCOO^(i)C₃H₇ 3-503 H F O CH₃ CF₃ H COCH₃ 3-504 H F O CH₃ CF₃ H COC₂H₅3-505 H Cl O CH₃ CF₃ H CH₂Br 3-506 H Cl O CH₃ CF₃ H CHBr₂ 3-507 H Cl OCH₃ CF₃ H CBr₃ 3-508 H Cl O CH₃ CF₃ H CHO 3-509 H Cl O CH₃ CF₃ H CN3-510 H Cl O CH₃ CF₃ H COOH 3-511 H Cl O CH₃ CF₃ H CH₂OH 3-512 H Cl OCH₃ CF₃ H CH₂OCH₃ 3-513 H Cl O CH₃ CF₃ H CH₂OC₂H₆ 3-514 H Cl O CH₃ CF₃ HCH₂O^(i)C₃H₇ 3-515 H Cl O CH₃ CF₃ H CH₂OCH₂OCH₃ 3-516 H Cl O CH₃ CF₃ HCH₂OCH₂OC₂H₅ 3-517 H Cl O CH₃ CF₃ H CH₂OCOCH₃ 3-518 H Cl O CH₃ CF₃ HCH₂OCOC₂H₅ 3-519 H Cl O CH₃ CF₃ H CH₂OCO^(i)C₃H₇ 3-520 H Cl O CH₃ CF₃ HCH₂OCOCH₂Cl 3-521 H Cl O CH₃ CF₃ H CH₂OCOCCl₃ 3-522 H Cl O CH₃ CF₃ HCH₂OCOCF₃ 3-523 H Cl O CH₃ CF₃ H COOCH₃ 3-524 H Cl O CH₃ CF₃ H COOC₂H₅3-525 H Cl O CH₃ CF₃ H COO^(n)C₃H₇ 3-526 H Cl O CH₃ CF₃ H COO^(n)C₄H₉3-527 H Cl O CH₃ CF₃ H COO^(n)C₅H₁₁ 3-528 H Cl O CH₃ CF₃ H COO^(i)C₃H₁₁3-529 H Cl O CH₃ CF₃ H COCH₃ 3-530 H Cl O CH₃ CF₃ H COC₂H₅ 3-531 F F OCH₃ CF₃ H CH₂Br 3-532 F F O CH₃ CF₃ H CHBr₂ 3-533 F F O CH₃ CF₃ H CBr₃3-534 F F O CH₃ CF₃ H CHO 3-535 F F O CH₃ CF₃ H CN 3-536 F F O CH₃ CF₃ HCOOH 3-537 F F O CH₃ CF₃ H CH₂OH 3-538 F F O CH₃ CF₃ H CH₂OCH₃ 3-539 F FO CH₃ CF₃ H CH₂OC₂H₅ 3-540 F F O CH₃ CF₃ H CH₂O^(i)C₃H₇ 3-541 F F O CH₃CF₃ H CH₂OCH₂OCH₃ 3-542 F F O CH₃ CF₃ H CH₂OCH₂OC₂H₅ 3-543 F F O CH₃ CF₃H CH₂OCOCH₃ 3-544 F F O CH₃ CF₃ H CH₂OCOC₂H₅ 3-545 F F O CH₃ CF₃ HCH₂OCO^(i)C₃H₇ 3-546 F F O CH₃ CF₃ H CH₂OCOCH₂Cl 3-547 F F O CH₃ CF₃ HCH₂OCOCCl₃ 3-548 F F O CH₃ CF₃ H CH₂OCOCF₃ 3-549 F F O CH₃ CF₃ H COOCH₃3-550 F F O CH₃ CF₃ H COOC₂H₅ 3-551 F F O CH₃ CF₃ H COO^(n)C₃H₇ 3-552 FF O CH₃ CF₃ H COO^(n)C₄H₉ 3-553 F F O CH₃ CF₃ H COO^(n)C₅H₁₁ 3-554 F F OCH₃ CF₃ H COO^(i)C₃H₇ 3-555 F F O CH₃ CF₃ H COCH₃ 3-556 F F O CH₃ CF₃ HCOC₂H₅ 3-557 F Cl O CH₃ CF₃ H CH₂Br 3-558 F Cl O CH₃ CF₃ H CHBr₂ 3-559 FCl O CH₃ CF₃ H CBr₃ 3-560 F Cl O CH₃ CF₃ H CHO 3-561 F Cl O CH₃ CF₃ H CN3-562 F Cl O CH₃ CF₃ H COOH 3-563 F Cl O CH₃ CF₃ H CH₂OH 3-564 F Cl OCH₃ CF₃ H CH₂OCH₃ 3-565 F Cl O CH₃ CF₃ H CH₂OC₂H₅ 3-566 F Cl O CH₃ CF₃ HCH₂O^(i)C₃H₇ 3-567 F Cl O CH₃ CF₃ H CH₂OCH₂OCH₃ 3-568 F Cl O CH₃ CF₃ HCH₂OCH₂OC₂H₅ 3-569 F Cl O CH₃ CF₃ H CH₂OCOCH₃ 3-570 F Cl O CH₃ CF₃ HCH₂OCOC₂H₅ 3-571 F Cl O CH₃ CF₃ H CH₂OCO^(i)C₃H₇ 3-572 F Cl O CH₃ CF₃ HCH₂OCOCH₂Cl 3-573 F Cl O CH₃ CF₃ H CH₂OCOCCl₃ 3-574 F Cl O CH₃ CF₃ HCH₂OCOCF₃ 3-575 F Cl O CH₃ CF₃ H COOCH₃ 3-576 F Cl O CH₃ CF₃ H COOC₂H₅3-577 F Cl O CH₃ CF₃ H COO^(n)C₃H₇ 3-578 F Cl O CH₃ CF₃ H COO^(n)C₄H₉3-579 F Cl O CH₃ CF₃ H COO^(n)C₅H₁₁ 3-580 F Cl O CH₃ CF₃ H COO^(i)C₃H₇3-581 F Cl O CH₃ CF₃ H COCH₃ 3-582 F Cl O CH₃ CF₃ H COC₂H₅

[0807] TABLE 4 Compounds of the formula

Com- pound No. X Y R³ R¹ R² R⁷ R⁸ 4-1 H Cl H CF₂Cl CH₃ H CH₂Cl 4-2 H ClH CF₂Cl CH₃ H CH₂Br 4-3 H Cl H CF₂Cl CH₃ H CH₂OCH₃ 4-4 H Cl H CF₂Cl CH₃H CH₂OC₂H₅ 4-5 H Cl H CF₂Cl CH₃ H CH₂OCH₂OCH₃ 4-6 H Cl H CF₂Cl CH₃ HCH₂OCH₂OC₂H₅ 4-7 H Cl H CF₂Cl CH₃ H CH₂OCOCH₃ 4-8 H Cl H CF₂Cl CH₃ HCH₂OCOC₂H₅ 4-9 H Cl H CF₂Cl CH₃ H CH₂OCO′C₃H₇ 4-10 H Cl H CF₂Cl CH₃ HCH₂OCOCH₂Cl 4-11 H Cl H CF₂Cl CH₃ H CH₂OCOCCl₃ 4-12 H Cl H CF₂Cl CH₃ HCH₂OCOCF₃ 4-13 H Cl H CF₂Cl CH₃ H COOH 4-14 H Cl H CF₂Cl CH₃ H COOCH₃4-15 H Cl H CF₂Cl CH₃ H COOC₂H₅ 4-16 H Cl H CF₂Cl CH₃ H COO^(n)C₃H₇ 4-17H Cl H CF₂Cl CH₃ H COO^(n)C₄H₉ 4-18 H Cl H CF₂Cl CH₃ H COO^(n)C₅H₁₁ 4-19H Cl H CF₂Cl CH₃ H COO′C₃H₇ 4-20 H Cl H CF₂Cl CH₃ H COO^(c)C₅H₉ 4-21 HCl H CF₂Cl CH₃ H COO^(c)C₆H₁₁ 4-22 H Cl H CF₂Cl CH₃ H COOCH₂CH═CH₂ 4-23H Cl H CF₂Cl CH₃ H COOCH₂ ⁻C≡CH₂ 4-24 H Cl H CF₂Cl CH₃ H CONH₂ 4-25 H ClH CF₂Cl CH₃ H CONHCH₃ 4-26 H Cl H CF₂Cl CH₃ H CONHC₂H₅ 4-27 H Cl H CF₂ClCH₃ H CON(CH₃)₂ 4-28 H Cl H CF₂Cl CH₃ H CON(C₂H₅)₂ 4-29 F Cl H CF₂Cl CH₃H CH₂Cl 4-30 F Cl H CF₂Cl CH₃ H CH₂Br 4-31 F Cl H CF₂Cl CH₃ H CH₂OCH₃4-32 F Cl H CF₂Cl CH₃ H CH₂OC₂H₅ 4-33 F Cl H CF₂Cl CH₃ H CH₂OCH₂OCH₃4-34 F Cl H CF₂Cl CH₃ H CH₂OCH₂OC₂H₅ 4-35 F Cl H CF₂Cl CH₃ H CH₂OCOCH₃4-36 F Cl H CF₂Cl CH₃ H CH₂OCOC₂H₅ 4-37 F Cl H CF₂Cl CH₃ H CH₂OCO′C₃H₇4-38 F Cl H CF₂Cl CH₃ H CH₂OCOCH₂Cl 4-39 F Cl H CF₂Cl CH₃ H CH₂OCOCCl₃4-40 F Cl H CF₂Cl CH₃ H CH₂OCOCF₃ 4-41 F Cl H CF₂Cl CH₃ H COOH 4-42 F ClH CF₂Cl CH₃ H COOCH₃ 4-43 F Cl H CF₂Cl CH₃ H COOC₂H₅ 4-44 F Cl H CF₂ClCH₃ H COO^(n)C₃H₇ 4-45 F Cl H CF₂Cl CH₃ H COO^(n)C₄H₉ 4-46 F Cl H CF₂ClCH₃ H COO^(n−)C₅H₁₁ 4-47 F Cl H CF₂Cl CH₃ H COO′C₃H₇ 4-48 F Cl H CF₂ClCH₃ H COO^(c)C₅H₉ 4-49 F Cl H CF₂Cl CH₃ H COO^(c)C₆H₁₁ 4-50 F Cl H CF₂ClCH₃ H COOCH₂CH═CH₂ 4-51 F Cl H CF₂Cl CH₃ H COOCH₂C≡CH 4-52 F Cl H CF₂ClCH₃ H CONH₂ 4-53 F Cl H CF₂Cl CH₃ H CONHCH₃ 4-54 F Cl H CF₂Cl CH₃ HCONHC₂H₅ 4-55 F Cl H CF₂Cl CH₃ H CON(CH₃)₂ 4-56 F Cl H CF₂Cl CH₃ HCON(C₂H₅)₂ 4-57 H Cl H CF₂Cl CH₃ CH₃ CH₂Cl 4-58 H Cl H CF₂Cl CH₃ CH₃CH₂Br 4-59 H Cl H CF₂Cl CH₃ CH₃ CH₂OCH₃ 4-60 H Cl H CF₂Cl CH₃ CH₃CH₂OC₂H₅ 4-61 H Cl H CF₂Cl CH₃ CH₃ CH₂OCH₂OCH₃ 4-62 H Cl H CF₂Cl CH₃ CH₃CH₂OCH₂OC₂H₅ 4-63 H Cl H CF₂Cl CH₃ CH₃ CH₂OCOCH₃ 4-64 H Cl H CF₂Cl CH₃CH₃ CH₂OCOC₂H₅ 4-65 H Cl H CF₂Cl CH₃ CH₃ CH₂OCO′C₃H₇ 4-66 H Cl H CF₂ClCH₃ CH₃ CH₂OCOCH₂Cl 4-67 H Cl H CF₂Cl CH₃ CH₃ CH₂OCOCCl₃ 4-68 H Cl HCF₂Cl CH₃ CH₃ CH₂OCOCF₃ 4-69 H Cl H CF₂Cl CH₃ CH₃ COOH⁻ 4-70 H Cl HCF₂Cl CH₃ CH₃ COOCH₃ 4-71 H Cl H CF₂Cl CH₃ CH₃ COOC₂H₅ 4-72 H Cl H CF₂ClCH₃ CH₃ COO^(n)C₃H₇ 4-73 H Cl H CF₂Cl CH₃ CH₃ COO^(n)C₄H₉ 4-74 H Cl HCF₂Cl CH₃ CH₃ COO^(n)C₅H₁₁ 4-75 H Cl H CF₂Cl CH₃ CH₃ COO′C₃H₇ 4-76 H ClH CF₂Cl CH₃ CH₃ COO^(c)C₅H₉ 4-77 H Cl H CF₂Cl CH₃ CH₃ COO^(n)C₆H₁₁ 4-78H Cl H CF₂Cl CH₃ CH₃ COOCH₂CH═CH₂ 4-79 H Cl H CF₂Cl CH₃ CH₃ COOCH₂C≡CH4-80 H Cl H CF₂Cl CH₃ CH₃ CONH₂ 4-81 H Cl H CF₂Cl CH₃ CH₃ CONHCH₃ 4-82 HCl H CF₂Cl CH₃ CH₃ CONHC₂H₅ 4-83 H Cl H CF₂Cl CH₃ CH₃ CON(CH₃)₂ 4-84 HCl H CF₂Cl CH₃ CH₃ CON(C₂H₅)₂ 4-85 F Cl H CF₂Cl CH₃ CH₃ CH₂Cl 4-86 F ClH CF₂Cl CH₃ CH₃ CH₂Br 4-87 F Cl H CF₂Cl CH₃ CH₃ CH₂OCH₃ 4-88 F Cl HCF₂Cl CH₃ CH₃ CH₂OC₂H₅ 4-89 F Cl H CF₂Cl CH₃ CH₃ CH₂OCH₂OCH₃ 4-90 F Cl HCF₂Cl CH₃ CH₃ CH₂OCH₂OC₂H₅ 4-91 F Cl H CF₂Cl CH₃ CH₃ CH₂OCOCH₃ 4-92 F ClH CF₂Cl CH₃ CH₃ CH₂OCOC₂H₅ 4-93 F Cl H CF₂Cl CH₃ CH₃ CH₂OCO′C₃H₇ 4-94 FCl H CF₂Cl CH₃ CH₃ CH₂OCOCH₂Cl 4-95 F Cl H CF₂Cl CH₃ CH₃ CH₂OCOCCl₃ 4-96F Cl H CF₂Cl CH₃ CH₃ CH₂OCOCF₃ 4-97 F Cl H CF₂Cl CH₃ CH₃ COOH 4-98 F ClH CF₂Cl CH₃ CH₃ COOCH₃ 4-99 F Cl H CF₂Cl CH₃ CH₃ COOC₂H₅ 4-100 F Cl HCF₂Cl CH₃ CH₃ COO^(n)C₃H₇ 4-101 F Cl H CF₂Cl CH₃ CH₃ COO^(n)C₄H₉ 4-102 FCl H CF₂Cl CH₃ CH₃ COO^(n)C₅H₁₁ 4-103 F Cl H CF₂Cl CH₃ CH₃ COO′C₃H₇4-104 F Cl H CF₂Cl CH₃ CH₃ COO^(c)C₅H₉ 4-105 F Cl H CF₂Cl CH₃ CH₃COO^(c)C₆H₁₁ 4-106 F Cl H CF₂Cl CH₃ CH₃ COOCH₂CH═CH₂ 4-107 F Cl H CF₂ClCH₃ CH₃ COOCH₂C≡CH 4-108 F Cl H CF₂Cl CH₃ CH₃ CONH₂ 4-109 F Cl H CF₂ClCH₃ CH₃ CONHCH₃ 4-110 F Cl H CF₂Cl CH₃ CH₃ CONHC₂H₅ 4-111 F Cl H CF₂ClCH₃ CH₃ CON(CH₃)₂ 4-112 F Cl H CF₂Cl CH₃ CH₃ CON(C₂H₅)₂ 4-113 H Cl H CF₃CH₃ H CH₂Cl 4-114 H Cl H CF₃ CH₃ H CH₂Br 4-115 H Cl H CF₃ CH₃ H CH₂OCH₃4-116 H Cl H CF₃ CH₃ H CH₂OC₂H₅ 4-117 H Cl H CF₃ CH₃ H CH₂OCH₂OCH₃ 4-118H Cl H CF₃ CH₃ H CH₂OCH₂OC₂H₅ 4-119 H Cl H CF₃ CH₃ H CH₂OCOCH₃ 4-120 HCl H CF₃ CH₃ H CH₂OCOC₂H₅ 4-121 H Cl H CF₃ CH₃ H CH₂OCO′C₃H₇ 4-122 H ClH CF₃ CH₃ H CH₂OCOCH₂Cl 4-123 H Cl H CF₃ CH₃ H CH₂OCOCCl₃ 4-124 H Cl HCF₃ CH₃ H CH₂OCOCF₃ 4-125 H Cl H CF₃ CH₃ H COOH 4-126 H Cl H CF₃ CH₃ HCOOCH₃ 4-127 H Cl H CF₃ CH₃ H COOC₂H₅ 4-128 H Cl H CF₃ CH₃ H COO^(n)C₃H₇4-129 H Cl H CF₃ CH₃ H COO^(n)C₄H₉ 4-130 H Cl H CF₃ CH₃ H COO^(n)C₅H₁₁4-131 H Cl H CF₃ CH₃ H COO′C₃H₇ 4-132 H Cl H CF₃ CH₃ H COO^(c)C₅H₉ 4-133H Cl H CF₃ CH₃ H COO^(c)C₆H₁₁ 4-134 H Cl H CF₃ CH₃ H COOCH₂CH═CH₂ 4-135H Cl H CF₃ CH₃ H COOCH₂C≡CH 4-136 H Cl H CF₃ CH₃ H CONH₂ 4-137 H Cl HCF₃ CH₃ H CONHCH₃ 4-138 H Cl H CF₃ CH₃ H CONHC₂H₅ 4-139 H Cl H CF₃ CH₃ HCON(CH₃)₂ 4-140 H Cl H CF₃ CH₃ H CON(C₂H₅)₂ 4-141 F Cl H CF₃ CH₃ H CH₂Cl4-142 F Cl H CF₃ CH₃ H CH₂Br 4-143 F Cl H CF₃ CH₃ H CH₂OCH₃ 4-144 F Cl HCF₃ CH₃ H CH₂OC₂H₅ 4-145 F Cl H CF₃ CH₃ H CH₂OCH₂OCH₃ 4-146 F Cl H CF₃CH₃ H CH₂OCH₂OC₂H₅ 4-147 F Cl H CF₃ CH₃ H CH₂OCOCH₃ 4-148 F Cl H CF₃ CH₃H CH₂OCOC₂H₅ 4-149 F Cl H CF₃ CH₃ H CH₂OCO′C₃H₇ 4-150 F Cl H CF₃ CH₃ HCH₂OCOCH₂Cl 4-151 F Cl H CF₃ CH₃ H CH₂OCOCCl₃ 4-152 F Cl H CF₃ CH₃ HCH₂OCOCF₃ 4-153 F Cl H CF₃ CH₃ H COOH 4-154 F Cl H CF₃ CH₃ H COOCH₃4-155 F Cl H CF₃ CH₃ H COOC₂H₅ 4-156 F Cl H CF₃ CH₃ H COO^(n)C₃H₇ 4-157F Cl H CF₃ CH₃ H COO^(n)C₄H₉ 4-158 F Cl H CF₃ CH₃ H COO^(n)C₅H₁₁ 4-159 FCl H CF₃ CH₃ H COO′C₃H₇ 4-160 F Cl H CF₃ CH₃ H COO^(c−)C₅H₉ 4-161 F Cl HCF₃ CH₃ H COO^(c)C₆H₁₁ 4-162 F Cl H CF₃ CH₃ H COOCH₂CH═CH₂ 4-163 F Cl HCF₃ CH₃ H COOCH₂C≡CH 4-164 F Cl H CF₃ CH₃ H CONH₂ 4-165 F Cl H CF₃ CH₃ HCONHCH₃ 4-166 F Cl H CF₃ CH₃ H CONHC₂H₅ 4-167 F Cl H CF₃ CH₃ H CON(CH₃)₂4-168 F Cl H CF₃ CH₃ H CON(C₂H₅)₂ 4-169 H Cl H CF₃ CH₃ CH₃ CH₂Cl 4-170 HCl H CF₃ CH₃ CH₃ CH₂Br 4-171 H Cl H CF₃ CH₃ CH₃ CH₂OCH₃ 4-172 H Cl H CF₃CH₃ CH₃ CH₂OC₂H₅ 4-173 H Cl H CF₃ CH₃ CH₃ CH₂OCH₂OCH₃ 4-174 H Cl H CF₃CH₃ CH₃ CH₂OCH₂OC₂H₅ 4-175 H Cl H CF₃ CH₃ CH₃ CH₂OCOCH₃ 4-176 H Cl H CF₃CH₃ CH₃ CH₂OCOC₂H₅ 4-177 H Cl H CF₃ CH₃ CH₃ CH₂OCO′C₃H₇ 4-178 H Cl H CF₃CH₃ CH₃ CH₂OCOCH₂Cl 4-179 H Cl H CF₃ CH₃ CH₃ CH₂OCOCCl₃ 4-180 H Cl H CF₃CH₃ CH₃ CH₂OCOCF₃ 4-181 H Cl H CF₃ CH₃ CH₃ COOH 4-182 H Cl H CF₃ CH₃ CH₃COOCH₃ 4-183 H Cl H CF₃ CH₃ CH₃ COOC²⁻H₅ 4-184 H Cl H CF₃ CH₃ CH₃COO^(n)C₃H₇ 4-185 H Cl H CF₃ CH₃ CH₃ COO^(n)C₄H₉ 4-186 H Cl H CF₃ CH₃CH₃ COO^(n)C₅H₁₁ 4-187 H Cl H CF₃ CH₃ CH₃ COO′C₃H₇ 4-188 H Cl H CF₃ CH₃CH₃ COO^(c)C₅H₉ 4-189 H Cl H CF₃ CH₃ CH₃ COO^(c)C₆H₁₁ 4-190 H Cl H CF₃CH₃ CH₃ COOCH₂CH═CH₂ 4-191 H Cl H CF₃ CH₃ CH₃ COOCH₂C≡CH 4-192 H Cl HCF₃ CH₃ CH₃ CONH₂ 4-193 H Cl H CF₃ CH₃ CH₃ CONHCH₃ 4-194 H Cl H CF₃ CH₃CH₃ CONHC₂H₅ 4-195 H Cl H CF₃ CH₃ CH₃ CON(CH₃)₂ 4-196 H Cl H CF₃ CH₃ CH₃CON(C₂H₅)₂ 4-197 F Cl H CF₃ CH₃ CH₃ CH₂Cl 4-198 F Cl H CF₃ CH₃ CH₃ CH₂Br4-199 F Cl H CF₃ CH₃ CH₃ CH₂OCH₃ 4-200 F Cl H CF₃ CH₃ CH₃ CH₂OC₂H₅ 4-201F Cl H CF₃ CH₃ CH₃ CH₂OCH₂OCH₃ 4-202 F Cl H CF₃ CH₃ CH₃ CH₂OCH₂OC₂H₅4-203 F Cl H CF₃ CH₃ CH₃ CH₂OCOCH₃ 4-204 F Cl H CF₃ CH₃ CH₃ CH₂OCOC₂H₅4-205 F Cl H CF₃ CH₃ CH₃ CH₂OCO′C₃H₇ 4-206 F Cl H CF₃ CH₃ CH₃CH₂OCOCH₂Cl 4-207 F Cl H CF₃ CH₃ CH₃ CH₂OCOCCl₃ 4-208 F Cl H CF₃ CH₃ CH₃CH₂OCOCF₃ 4-209 F Cl H CF₃ CH₃ CH₃ COOH 4-210 F Cl H CF₃ CH₃ CH₃ COOCH₃4-211 F Cl H CF₃ CH₃ CH₃ COOC₂H₅ 4-212 F Cl H CF₃ CH₃ CH₃ COO^(n)C₃H₇4-213 F Cl H CF₃ CH₃ CH₃ COO^(n)C₄H₉ 4-214 F Cl H CF₃ CH₃ CH₃COO^(n)C₅H₁₁ 4-215 F Cl H CF₃ CH₃ CH₃ COO′C₃H₇ 4-216 F Cl H CF₃ CH₃ CH₃COO^(c)C₅H₉ 4-217 F Cl H CF₃ CH₃ CH₃ COO^(c)C₆H₁₁ 4-218 F Cl H CF₃ CH₃CH₃ COOCH₂CH═CH₂ 4-219 F Cl H CF₃ CH₃ CH₃ COOCH₂C≡CH 4-220 F Cl H CF₃CH₃ CH₃ CONH₂ 4-221 F Cl H CF₃ CH₃ CH₃ CONHCH₃ 4-222 F Cl H CF₃ CH₃ CH₃CONHC₂H₅ 4-223 F Cl H CF₃ CH₃ CH₃ CON(CH₃)₂ 4-224 F Cl H CF₃ CH₃ CH₃CON(C₂H₅)₂ 4-225 H Cl H CF₂Cl CH₃ H CH₂Cl 4-226 H Cl H CF₂Cl CH₃ H CH₂Br4-227 H Cl H CF₂Cl CH₃ H CH₂OCH₃ 4-228 H Cl H CF₂Cl CH₃ H CH₂OC₂H₅ 4-229H Cl H CF₂Cl CH₃ H CH₂OCH₂OCH₃ 4-230 H Cl H CF₂Cl CH₃ H CH₂OCH₂OC₂H₅4-231 H Cl H CF₂Cl CH₃ H CH₂OCOCH₃ 4-232 H Cl H CF₂Cl CH₃ H CH₂OCOC₂H₅4-233 H Cl H CF₂Cl CH₃ H CH₂OCO′C₃H₇ 4-234 H Cl H CF₂Cl CH₃ HCH₂OCOCH₂Cl 4-235 H Cl H CF₂Cl CH₃ H CH₂OCOCCl₃ 4-236 H Cl H CF₂Cl CH₃ HCH₂OCOCF₃ 4-237 H Cl H CF₂Cl CH₃ H COOH 4-238 H Cl H CF₂Cl CH₃ H COOCH₃4-239 H Cl H CF₂Cl CH₃ H COOC₂H₅ 4-240 H Cl H CF₂Cl CH₃ H COO^(n)C₃H₇4-241 H Cl H CF₂Cl CH₃ H COO^(n)C₄H₉ 4-242 H Cl H CF₂Cl CH₃ HCOO^(n)C₅H₁₁ 4-243 H Cl H CF₂Cl CH₃ H COO′C₃H₇ 4-244 H Cl H CF₂Cl CH₃ HCOO^(c)C₅H₉ 4-245 H Cl H CF₂Cl CH₃ H COO^(c)C₆H₁₁ 4-246 H Cl H CF₂Cl CH₃H COOCH₂CH═CH₂ 4-247 H Cl H CF₂Cl CH₃ H COOCH₂C≡CH 4-248 H Cl H CF₂ClCH₃ H CONH₂ 4-249 H Cl H CF₂Cl CH₃ H CONHCH₃ 4-250 H Cl H CF₂Cl CH₃ HCONHC₂H₅ 4-251 H Cl H CF₂Cl CH₃ H CON(CH₃)₂ 4-252 H Cl H CF₂Cl CH₃ HCON(C₂H₅)₂ 4-253 F Cl H CF₂Cl CH₃ H CH₂Cl 4-254 F Cl H CF₂Cl CH₃ H CH₂Br4-255 F Cl H CF₂Cl CH₃ H CH₂OCH₃ 4-256 F Cl H CF₂Cl CH₃ H CH₂OC₂H₅ 4-257F Cl H CF₂Cl CH₃ H CH₂OCH₂OCH₃ 4-258 F Cl H CF₂Cl CH₃ H CH₂OCH₂OC₂H₅4-259 F Cl H CF₂Cl CH₃ H CH₂OCOCH₃ 4-260 F Cl H CF₂Cl CH₃ H CH₂OCOC₂H₅4-261 F Cl H CF₂Cl CH₃ H CH₂OCO′C₃H₇ 4-262 F Cl H CF₂Cl CH₃ HCH₂OCOCH₂Cl 4-263 F Cl H CF₂Cl CH₃ H CH₂OCOCCl₃ 4-264 F Cl H CF₂Cl CH₃ HCH₂OCOCF₃ 4-265 F Cl H CF₂Cl CH₃ H COOH 4-266 F Cl H CF₂Cl CH₃ H COOCH₃4-267 F Cl H CF₂Cl CH₃ H COOC₂H₅ 4-268 F Cl H CF₂Cl CH₃ H COO^(n)C₃H₇4-269 F Cl H CF₂Cl CH₃ H COO^(n)C₄H₉ 4-270 F Cl H CF₂Cl CH₃ HCOO^(n)C₅H₁₁ 4-271 F Cl H CF₂Cl CH₃ H COO′C₃H₇ 4-272 F Cl H CF₂Cl CH₃ HCOO^(c)C₅H₉ 4-273 F Cl H CF₂Cl CH₃ H COO^(c)C₆H₁₁ 4-274 F Cl H CF₂Cl CH₃H COOCH²⁻CH═CH₂ 4-275 F Cl H CF₂Cl CH₃ H COOCH₂C≡CH 4-276 F Cl H CF₂ClCH₃ H CONH₂ 4-277 F Cl H CF₂Cl CH₃ H CONHCH₃ 4-278 F Cl H CF₂Cl CH₃ HCONHC₂H₅ 4-279 F Cl H CF₂Cl CH₃ H CON(CH₃)₂ 4-280 F Cl H CF₂Cl CH₃ HCON(C₂H₅)₂ 4-281 H Cl H CF₂Cl CH₃ CH₃ CH₂Cl 4-282 H Cl H CF₂Cl CH₃ CH₃CH₂Br 4-283 H Cl H CF₂Cl CH₃ CH₃ CH₂OCH₃ 4-284 H Cl H CF₂Cl CH₃ CH₃CH₂OC₂H₅ 4-285 H Cl H CF₂Cl CH₃ CH₃ CH₂OCH₂OCH₃ 4-286 H Cl H CF₂Cl CH₃CH₃ CH₂OCH₂OC₂H₅ 4-287 H Cl H CF₂Cl CH₃ CH₃ CH₂OCOCH₃ 4-288 H Cl H CF₂ClCH₃ CH₃ CH₂OCOCH₂H₅ 4-289 H Cl H CF₂Cl CH₃ CH₃ CH₂OCO′C₃H₇ 4-290 H Cl HCF₂Cl CH₃ CH₃ CH₂OCOCH₂Cl 4-291 H Cl H CF₂Cl CH₃ CH₃ CH₂OCOCCl₃ 4-292 HCl H CF₂Cl CH₃ CH₃ CH₂OCOCF₃ 4-293 H Cl H CF₂Cl CH₃ CH₃ COOH 4-294 H ClH CF₂Cl CH₃ CH₃ COOCH₃ 4-295 H Cl H CF₂Cl CH₃ CH₃ COOC₂H₅ 4-296 H Cl HCF₂Cl CH₃ CH₃ COO^(n)C₃H₇ 4-297 H Cl H CF₂Cl CH₃ CH₃ COO^(n−)C₄H₉ 4-298H Cl H CF₂Cl CH₃ CH₃ COO^(n)C₅H₁₁ 4-299 H Cl H CF₂Cl CH₃ CH₃ COO′C₃H₇4-300 H Cl H CF₂Cl CH₃ CH₃ COO^(c)C₅H₉ 4-301 H Cl H CF₂Cl CH₃ CH₃COO^(c)C₆H₁₁ 4-302 H Cl H CF₂Cl CH₃ CH₃ COOCH₂CH═CH₂ 4-303 H Cl H CF₂ClCH₃ CH₃ COOCH₂C≡CH 4-304 H Cl H CF₂Cl CH₃ CH₃ CONH₂ 4-305 H Cl H CF₂ClCH₃ CH₃ CONHCH₃ 4-306 H Cl H CF₂Cl CH₃ CH₃ CONHC₂H₅ 4-307 H Cl H CF₂ClCH₃ CH₃ CON(CH₃)₂ 4-308 H Cl H CF₂Cl CH₃ CH₃ CON(C₂H₅)₂ 4-309 F Cl HCF₂Cl CH₃ CH₃ CH₂Cl 4-310 F Cl H CF₂Cl CH₃ CH₃ CH₂Br 4-311 F Cl H CF₂ClCH₃ CH₃ CH₂OCH₃ 4-312 F Cl H CF₂Cl CH₃ CH₃ CH₂OC₂H₆ 4-313 F Cl H CF₂ClCH₃ CH₃ CH₂OCH₂OCH₃ 4-314 F Cl H CF₂Cl CH₃ CH₃ CH₂OCH₂OC₂H₅ 4-315 F Cl HCF₂Cl CH₃ CH₃ CH₂OCOCH₃ 4-316 F Cl H CF₂Cl CH₃ CH₃ CH₂OCOC₂H₅ 4-317 F ClH CF₂Cl CH₃ CH₃ CH₂OCO′C₃H₇ 4-318 F Cl H CF₂Cl CH₃ CH₃ CH₂OCOCH₂Cl 4-319F Cl H CF₂Cl CH₃ CH₃ CH₂OCOCCl₃ 4-320 F Cl H CF₂Cl CH₃ CH₃ CH₂OCOCF₃4-321 F Cl H CF₂Cl CH₃ CH₃ COOH 4-322 F Cl H CF₂Cl CH₃ CH₃ COOCH₃ 4-323F Cl H CF₂Cl CH₃ CH₃ COOC₂H₅ 4-324 F Cl H CF₂Cl CH₃ CH₃ COO^(n)C₃H₇4-325 F Cl H CF₂Cl CH₃ CH₃ COO^(n)C₄H₉ 4-326 F Cl H CF₂Cl CH₃ CH₃COO^(n)C₅H₁₁ 4-327 F Cl H CF₂Cl CH₃ CH₃ COO′C₃H₇ 4-328 F Cl H CF₂Cl CH₃CH₃ COO^(c)C₅H₉ 4-329 F Cl H CF₂Cl CH₃ CH₃ COO^(c)C₆H₁₁ 4-330 F Cl HCF₂Cl CH₃ CH₃ COOCH₂CH═CH₂ 4-331 F Cl H CF₂Cl CH₃ CH₃ COOCH₂C≡CH 4-332 FCl H CF₂Cl CH₃ CH₃ CONH₂ 4-333 F Cl H CF₂Cl CH₃ CH₃ CONHCH₃ 4-334 F Cl HCF₂Cl CH₃ CH₃ CONHC₂H₅ 4-335 F Cl H CF₂Cl CH₃ CH₃ CON(CH₃)₂ 4-336 F Cl HCF₂Cl CH₃ CH₃ CON(C₂H₅)₂ 4-337 H Cl H CF₃ CH₃ H CH₂Cl 4-338 H Cl H CF₃CH₃ H CH₂Br 4-339 H Cl H CF₃ CH₃ H CH₂OCH₃ 4-340 H Cl H CF₃ CH₃ HCH₂OC₂H₅ 4-341 H Cl H CF₃ CH₃ H CH₂OCH₂OCH₃ 4-342 H Cl H CF₃ CH₃ HCH₂OCH₂OC₂H₅ 4-343 H Cl H CF₃ CH₃ H CH₂OCOCH₃ 4-344 H Cl H CF₃ CH₃ HCH₂OCOC₂H₅ 4-345 H Cl H CF₃ CH₃ H CH₂OCO′C₃H₇ 4-346 H Cl H CF₃ CH₃ HCH₂OCOCH₂Cl 4-347 H Cl H CF₃ CH₃ H CH₂OCOCCl₃ 4-348 H Cl H CF₃ CH₃ HCH₂OCOCF₃ 4-349 H Cl H CF₃ CH₃ H COOH 4-350 H Cl H CF₃ CH₃ H COOCH₃4-351 H Cl H CF₃ CH₃ H COOC₂H₅ 4-352 H Cl H CF₃ CH₃ H COO^(n)C₃H₇ 4-353H Cl H CF₃ CH₃ H COO^(n)C₄H₉ 4-354 H Cl H CF₃ CH₃ H COO^(n)C₅H₁₁ 4-355 HCl H CF₃ CH₃ H COO′C₃H₇ 4-356 H Cl H CF₃ CH₃ H COO^(c)C₅H₉ 4-357 H Cl HCF₃ CH₃ H COO^(c)C₆H₁₁ 4-358 H Cl H CF₃ CH₃ H COOCH₂CH═CH₂ 4-359 H Cl HCF₃ CH₃ H COOCH₂C≡CH 4-360 H Cl H CF₃ CH₃ H CONH₂ 4-361 H Cl H CF₃ CH₃ HCONHCH₃ 4-362 H Cl H CF₃ CH₃ H CONHC₂H₅ 4-363 H Cl H CF₃ CH₃ H CON(CH₃)₂4-364 H Cl H CF₃ CH₃ H CON(C₂H₅₎ ₂ 4-365 F Cl H CF₃ CH₃ H CH₂Cl⁻ 4-366 FCl H CF₃ CH₃ H CH₂Br 4-367 F Cl H CF₃ CH₃ H CH₂OCH₃ 4-368 F Cl H CF₃ CH₃H CH₂OC₂H₅ 4-369 F Cl H CF₃ CH₃ H CH₂OCH₂OCH₃ 4-370 F Cl H CF₃ CH₃ HCH₂OCH₂OC₂H₅ 4-371 F Cl H CF₃ CH₃ H CH₂OCOCH₃ 4-372 F Cl H CF₃ CH₃ HCH₂OCOC₂H₅ 4-373 F Cl H CF₃ CH₃ H CH₂OCO′C₃H₇ 4-374 F Cl H CF₃ CH₃ HCH₂OCOCH₂Cl 4-375 F Cl H CF₃ CH₃ H CH₂OCOCCl₃ 4-376 F Cl H CF₃ CH₃ HCH₂OCOCF₃ 4-377 F Cl H CF₃ CH₃ H COOH 4-378 F Cl H CF₃ CH₃ H COOCH₃4-379 F Cl H CF₃ CH₃ H COOC₂H₅ 4-380 F Cl H CF₃ CH₃ H COO^(n)C₃H₇ 4-381F Cl H CF₃ CH₃ H COO^(n)C₄H₉ 4-382 F Cl H CF₃ CH₃ H COO^(n)C₅H₁₁ 4-383 FCl H CF₃ CH₃ H COO′C₃H₇ 4-384 F Cl H CF₃ CH₃ H COO^(c)C₅H₉ 4-385 F Cl HCF₃ CH₃ H COO^(c)C₆H₁₁ 4-386 F Cl H CF₃ CH₃ H COOCH₂CH═CH₂ 4-387 F Cl HCF₃ CH₃ H COOCH₂C≡CH 4-388 F Cl H CF₃ CH₃ H CONH₂ ⁻ 4-389 F Cl H CF₃ CH₃H CONHCH₃ 4-390 F Cl H CF₃ CH₃ H CONHC₂H₅ 4-391 F Cl H CF₃ CH₃ HCON(CH₃)₂ 4-392 F Cl H CF₃ CH₃ H CON(C₂H₅)₂ 4-393 H Cl H CF₃ CH₃ CH₃CH₂Cl 4-394 H Cl H CF₃ CH₃ CH₃ CH₂Br 4-395 H Cl H CF₃ CH₃ CH₃ CH₂OCH₃4-396 H Cl H CF₃ CH₃ CH₃ CH₂OC₂H₅ 4-397 H Cl H CF₃ CH₃ CH₃ CH₂OCH₂OCH₃4-398 H Cl H CF₃ CH₃ CH₃ CH₂OCH₂OC₂H₅ 4-399 H Cl H CF₃ CH₃ CH₃ CH₂OCOCH₃4-400 H Cl H CF₃ CH₃ CH₃ CH₂OCOC₂H₅ 4-401 H Cl H CF₃ CH₃ CH₃ CH₂OCO′C₃H₇4-402 H Cl H CF₃ CH₃ CH₃ CH₂OCOCH₂Cl 4-403 H Cl H CF₃ CH₃ CH₃ CH₂OCOCCl₃4-404 H Cl H CF₃ CH₃ CH₃ CH₂OCOCF₃ 4-405 H Cl H CF₃ CH₃ CH₃ COOH 4-406 HCl H CF₃ CH₃ CH₃ COOCH₃ 4-407 H Cl H CF₃ CH₃ CH₃ COOC₂H₅ 4-408 H Cl HCF₃ CH₃ CH₃ COO^(n)C₃H₇ 4-409 H Cl H CF₃ CH₃ CH₃ COO^(n)C₄H₉ 4-410 H ClH CF₃ CH₃ CH₃ COO^(n)C₅H₁₁ 4-411 H Cl H CF₃ CH₃ CH₃ COO′C₃H₇ 4-412 H ClH CF₃ CH₃ CH₃ COO^(c)C₅H₉ 4-413 H Cl H CF₃ CH₃ CH₃ COO^(c)C₆H₁₁ 4-414 HCl H CF₃ CH₃ CH₃ COOCH₂CH═CH₂ 4-415 H Cl H CF₃ CH₃ CH₃ COOCH₂C≡CH 4-416H Cl H CF₃ CH₃ CH₃ CONH₂ 4-417 H Cl H CF₃ CH₃ CH₃ CONHCH₃ 4-418 H Cl HCF₃ CH₃ CH₃ CONHC₂H₅ 4-419 H Cl H CF₃ CH₃ CH₃ CON(CH₃)₂ 4-420 H Cl H CF₃CH₃ CH₃ CON(C₂H₅)₂ 4-421 F Cl H CF₃ CH₃ CH₃ CH₂Cl 4-422 F Cl H CF₃ CH₃CH₃ CH₂Br 4-423 F Cl H CF₃ CH₃ CH₃ CH₂OCH₃ 4-424 F Cl H CF₃ CH₃ CH₃CH₂OC₂H₅ 4-425 F Cl H CF₃ CH₃ CH₃ CH₂OCH₂OCH₃ 4-426 F Cl H CF₃ CH₃ CH₃CH₂OCH₂OC₂H₅ 4-427 F Cl H CF₃ CH₃ CH₃ CH₂OCOCH₃ 4-428 F Cl H CF₃ CH₃ CH₃CH₂OCOC₂H₅ 4-429 F Cl H CF₃ CH₃ CH₃ CH₂OCO′C₃H₇ 4-430 F Cl H CF₃ CH₃ CH₃CH₂OCOCH₂Cl 4-431 F Cl H CF₃ CH₃ CH₃ CH₂OCOCCl₃ 4-432 F Cl H CF₃ CH₃ CH₃CH₂OCOCF₃ 4-433 F Cl H CF₃ CH₃ CH₃ COOH 4-434 F Cl H CF₃ CH₃ CH₃ COOCH₃4-435 F Cl H CF₃ CH₃ CH₃ COOC₂H₅ 4-436 F Cl H CF₃ CH₃ CH₃ COO^(n)C₃H₇4-437 F Cl H CF₃ CH₃ CH₃ COO^(n)C₄H₉ 4-438 F Cl H CF₃ CH₃ CH₃COO^(n)C₁H₁₁ 4-439 F Cl H CF₃ CH₃ CH₃ COO′C₃H₇ 4-440 F Cl H CF₃ CH₃ CH₃COO^(c)C₅H₉ 4-441 F Cl H CF₃ CH₃ CH₃ COO^(c)C₆H₁₁ 4-442 F Cl H CF₃ CH₃CH₃ COOCH₂CH═CH₂ 4-443 F Cl H CF₃ CH₃ CH₃ COOCH₂C≡CH 4-444 F Cl H CF₃CH₃ CH₃ CONH₂ 4-445 F Cl H CF₃ CH₃ CH₃ CONHCH₃ 4-446 F Cl H CF₃ CH₃ CH₃CONHC₂H₅ 4-447 F Cl H CF₃ CH₃ CH₃ CON(CH₃)₂ 4-448 F Cl H CF₃ CH₃ CH₃CON(C₂H₅)₂ 4-449 F Cl H CF₃ CH₃ H CH₃ 4-450 F Cl H CF₃ CH₃ H CH₂OH 4-451F Cl H CF₃ CH₃ CH₃ CH₃ 4-452 F Cl H CF₃ CH₃ CH₃ CH₂OH 4-453 F Cl H CF₃ HH CH₃ 4-454 F Cl H CF₃ H H CH₂OH 4-455 F Cl H CF₃ H CH₃ CH₃ 4-456 F Cl HCF₃ H CH₃ CH₂OH 4-457 H Cl H CF₃ CH₃ H CH₃ 4-458 H Cl H CF₃ CH₃ H CH₂OH4-459 H Cl H CF₃ CH₃ CH₃ CH₃ 4-460 H Cl H CF₃ CH₃ CH₃ CH₂OH 4-461 H Cl HCF₃ H H CH₃ 4-462 H Cl H CF₃ H H CH₂OH 4-463 H Cl H CF₃ H CH₃ CH₃ 4-464H Cl H CF₃ H CH₃ CH₂OH 4-465 F Cl H CF₂Cl CH₃ H CH₃ 4-466 F Cl H CF₂ClCH₃ H CH₂OH 4-467 F Cl H CF₂Cl CH₃ CH₃ CH₃ 4-468 F Cl H CF₂Cl CH₃ CH₃CH₂OH 4-469 F Cl H CF₂Cl H H CH₃ 4-470 F Cl H CF₂Cl H H CH₂OH 4-471 F ClH CF₂Cl H CH₃ CH₃ 4-472 F Cl H CF₂Cl H CH₃ CH₂OH 4-473 H Cl H CF₂Cl CH₃H CH₃ 4-474 H Cl H CF₂Cl CH₃ H CH₂OH 4-475 H Cl H CF₂Cl CH₃ CH₃ CH₃4-476 H Cl H CF₂Cl CH₃ CH₃ CH₂OH 4-477 H Cl H CF₂Cl H H CH₃ 4-478 H Cl HCF₂Cl H H CH₂OH 4-479 H Cl H CF₂Cl H CH₃ CH₃ 4-480 H Cl H CF₂Cl H CH₃CH₂OH 4-481 H Cl H CF₃ H H CH₂Cl 4-482 H Cl H CF₃ H H CH₂Br 4-483 H Cl HCF₃ H H CH₂OCH₃ 4-484 H Cl H CF₃ H H CH₂OC₂H₅ 4-485 H Cl H CF₃ H HCH₂OCH₂OCH₃ 4-486 H Cl H CF₃ H H CH₂OCH₂OC₂H₅ 4-487 H Cl H CF₃ H HCH₂OCOCH₃ 4-488 H Cl H CF₃ H H CH₂OCOC₂H₅ 4-489 H Cl H CF₃ H HCH₂OCO′C₃H₇ 4-490 H Cl H CF₃ H H CH₂OCOCH₂Cl 4-491 H Cl H CF₃ H HCH₂OCOCCl₃ 4-492 H Cl H CF₃ H H CH₂OCOCF₃ 4-493 H Cl H CF₃ H H COOH4-494 H Cl H CF₃ H H COOCH₃ 4-495 H Cl H CF₃ H H COOC₂H₅ 4-496 H Cl HCF₃ H H COO^(n)C₃H₇ 4-497 H Cl H CF₃ H H COO^(n)C₄H₉ 4-498 H Cl H CF₃ HH COO^(n)C₅H₁₁ 4-499 H Cl H CF₃ H H COO′C₃H₇ 4-500 H Cl H CF₃ H HCOO^(c)C₅H₉ 4-501 H Cl H CF₃ H H COO^(c)C₆H₁₁ 4-502 H Cl H CF₃ H HCOOCH₂ ⁻CH═CH₂ 4-503 H Cl H CF₃ H H COOCH₂C≡CH 4-504 H Cl H CF₃ H HCONH₂ 4-505 H Cl H CF₃ H H CONHCH₃ 4-506 H Cl H CF₃ H H CONHC₂H₅ 4-507 HCl H CF₃ H H CON(CH₃)₂ 4-508 H Cl H CF₃ H H CON(C₂H₅)₂ 4-509 F Cl H CF₃H H CH₂Cl 4-510 F Cl H CF₃ H H CH₂Br 4-511 F Cl H CF₃ H H CH₂OCH₃ 4-512F Cl H CF₃ H H CH₂OC₂H₅ 4-513 F Cl H CF₃ H H CH₂OCH₂OCH₃ 4-514 F Cl HCF₃ H H CH₂OCH₂OC₂H₅ 4-515 F Cl H CF₃ H H CH₂OCOCH₃ 4-516 F Cl H CF₃ H HCH₂OCOC₂H₅ 4-517 F Cl H CF₃ H H CH₂OCO′C₃H₇ 4-518 F Cl H CF₃ H HCH₂OCOCH₂Cl 4-519 F Cl H CF₃ H H CH₂OCOCCl₃ 4-520 F Cl H CF₃ H HCH₂OCOCH₂Cl 4-521 F Cl H CF₃ H H CH₂OCOCCl₃ 4-522 F Cl H CF₃ H HCH₂OCOCF₃ 4-523 F Cl H CF₃ H H COOH 4-524 F Cl H CF₃ H H COOCH₃ 4-525 FCl H CF₃ H H COOC₂H₅ 4-526 F Cl H CF₃ H H COO^(n)C₃H₇ 4-527 F Cl H CF₃ HH COO^(n−)C₄H₉ 4-528 F Cl H CF₃ H H COO^(n)C₅H₁₁ 4-529 F Cl H CF₃ H HCOO′C₃H₇ 4-530 F Cl H CF₃ H H COO^(c)C₅H₉ 4-531 F Cl H CF₃ H HCOO^(n)C₆H₁₁ 4-532 F Cl H CF₃ H H COOCH₂CH═CH₂ 4-533 F Cl H CF₃ H HCOOCH₂C≡CH 4-534 F Cl H CF₃ H H CONHCH₃ 4-535 F Cl H CF₃ H H CON(CH₃)₂4-536 F Cl H CF₃ H H CON(C₂H₅)₂ 4-537 H Cl H CF₃ H CH₃ CH₂Cl 4-538 H ClH CF₃ H CH₃ CH₂Br 4-539 H Cl H CF₃ H CH₃ CH₂OCH₃ 4-540 H Cl H CF₃ H CH₃CH₂OC₂H₅ 4-541 H Cl H CF₃ H CH₃ CH₂OCH₂OCH₃ 4-542 H Cl H CF₃ H CH₃CH₂OCH₂OC₂H₅ 4-543 H Cl H CF₃ H CH₃ CH₂OCOCH₃ 4-544 H Cl H CF₃ H CH₃CH₂OCOC₂H₅ 4-545 H Cl H CF₃ H CH₃ CH₂OCO′C₃H₇ 4-546 H Cl H CF₃ H CH₃CH₂OCOCH₂Cl 4-547 H Cl H CF₃ H CH₃ CH₂OCOCCl₃ 4-548 H Cl H CF₃ H CH₃CH₂OCOCF₃ 4-549 H Cl H CF₃ H CH₃ COOH 4-550 H Cl H CF₃ H CH₃ COOCH₃4-551 H Cl H CF₃ H CH₃ COOC₂H₅ 4-552 H Cl H CF₃ H CH₃ COO^(n)C₃H₇ 4-553H Cl H CF₃ H CH₃ COO^(n)C₄H₉ 4-554 H Cl H CF₃ H CH₃ COO^(n)C₅H₁₁ 4-555 HCl H CF₃ H CH₃ COO^(′C) ₃H₇ 4-556 H Cl H CF₃ H CH₃ COO^(c)C₅H₉ 4-557 HCl H CF₃ H CH₃ COO^(c)C₆H₁₁ 4-558 H Cl H CF₃ H CH₃ COOCH₂CH═CH₂ 4-559 HCl H CF₃ H CH₃ COOCH₂C≡CH 4-560 H Cl H CF₃ H CH₃ CONH₂ 4-561 H Cl H CF₃H CH₃ CONHCH₃ 4-562 H Cl H CF₃ H CH₃ CONHC₂H₅ 4-563 H C H CF₃ H CH₃CON(CH₃)₂ 4-564 H C H CF₃ H CH₃ CON(C₂H₅)₂ 4-565 F Cl H CF₃ H CH₃ CH₂Cl4-566 F Cl H CF₃ H CH₃ CH₂Br 4-567 F Cl H CF₃ H CH₃ CH₂OCH₃ 4-568 F Cl HCF₃ H CH₃ CH₂OC₂H₅ 4-569 F Cl H CF₃ H CH₃ CH₂OCH₂OCH₃ 4-570 F Cl H CF₃ HCH₃ CH₂OCH²⁻OC₂H₅ 4-571 F Cl H CF₃ H CH₃ CH₂OCOCH₃ 4-572 F Cl H CF₃ HCH₃ CH₂OCOC₂H₅ 4-573 F Cl H CF₃ H CH₃ CH₂OCO′C₃H₇ 4-574 F Cl H CF₃ H CH₃CH₂OCOCH₂Cl 4-575 F Cl H CF₃ H CH₃ CH₂OCOCCl₃ 4-576 F Cl H CF₃ H CH₃CH₂OCOCF₃ 4-577 F Cl H CF₃ H CH₃ COOH 4-578 F Cl H CF₃ H CH₃ COOCH₃4-579 F Cl H CF₃ H CH₃ COOC₂H₅ 4-580 F Cl H CF₃ H CH₃ COO^(n)C₃H₇ 4-581F Cl H CF₃ H CH₃ COO^(n−)C₄H₉ 4-582 F Cl H CF₃ H CH₃ COO^(n)C₅H₁₁ 4-583F Cl H CF₃ H CH₃ COO′C₃H₇ 4-584 F Cl H CF₃ H CH₃ COO^(c)C₅H₉ 4-585 F ClH CF₃ H CH₃ COO^(n)C₆H₁₁ 4-586 F Cl H CF₃ H CH₃ COOCH₂═CH₂ 4-587 F Cl HCF₃ H CH₃ COOCH₂C≡CH 4-588 F Cl H CF₃ H CH₃ CONH₂ 4-589 F Cl H CF₃ H CH₃CONHCH₃ 4-590 F Cl H CF₃ H CH₃ CONHC₂H₅ 4-591 F Cl H CF₃ H CH₃ CON(CH₃)₂4-592 F Cl H CF₃ H CH₃ CON(C₂H₅)₂ 4-593 H Cl H CF₃ H H CH₂Cl⁻ 4-594 H ClH CF₃ H H CH₂Br 4-595 H Cl H CF₃ H H CH₂OCH₃ 4-596 H Cl H CF₃ H HCH₂OC₂H₅ 4-597 H Cl H CF₃ H H CH₂OCH₂OCH₅ 4-598 H Cl H CF₃ H HCH₂OCH₂OC₂H₅ 4-599 H Cl H CF₃ H H CH₂OCOCH₃ 4-600 H Cl H CF₃ H HCH₂OCOC₂H₅ 4-601 H Cl H CF₃ H H CH₂OCO′C₃H₇ 4-602 H Cl H CF₃ H HCH₂OCOCH₂Cl 4-603 H Cl H CF₃ H H CH₂OCOCCl₃ 4-604 H Cl H CF₃ H HCH₂OCOCF₃ 4-605 H Cl H CF₃ H H COOH 4-606 H Cl H CF₃ H H COOCH₃ 4-607 HCl H CF₃ H H COOC₂H₅ 4-608 H Cl H CF₃ H H COO^(n)C₃H₇ 4-609 H Cl H CF₃ HH COO^(n)C₄H₉ 4-610 H Cl H CF₃ H H COO^(n)C₅H₁₁ 4-611 H Cl H CF₃ H HCOO′C₃H₇ 4-612 H Cl H CF₃ H H COO^(c)C₅H₉ 4-613 H Cl H CF₃ H HCOO^(c)C₆H₁₁ 4-614 H Cl H CF₃ H H COOCH₂CH═CH₂ 4-615 H Cl H CF₃ H HCOOCH₂C≡CH 4-616 H Cl H CF₃ H H CONH₂ ⁻ 4-617 H Cl H CF₃ H H CONHCH₃4-618 H Cl H CF₃ H H CONHC₂H₅ 4-619 H Cl H CF₃ H H CON(CH₃)₂ 4-620 H ClH CF₃ H H CON(C₂H₅)₂ 4-621 F Cl H CF₃ H H CH₂Cl 4-622 F Cl H CF₃ H HCH₂Br 4-623 F Cl H CF₃ H H CH₂OCH₃ 4-624 F Cl H CF₃ H H CH₂OC₂H₅ 4-625 FCl H CF₃ H H CH₂OCH₂OCH₃ 4-626 F Cl H CF₃ H H CH₂OCH₂OC₂H₅ 4-627 F Cl HCF₃ H H CH₂OCOCH₃ 4-628 F Cl H CF₃ H H CH₂OCOC₂H₅ 4-629 F Cl H CF₃ H HCH₂OCO′C₃H₇ 4-630 F Cl H CF₃ H H CH₂OCOCH₂Cl 4-631 F Cl H CF₃ H HCH₂OCOCCl₃ 4-632 F Cl H CF₃ H H CH₂OCOCF₃ 4-633 F Cl H CF₃ H H COOH4-634 F Cl H CF₃ H H COOCH₃ 4-635 F Cl H CF₃ H H COOC₂H₅ 4-636 F Cl HCF₃ H H COO^(n)C₃H₇ 4-637 F Cl H CF₃ H H COO^(n)C₄H₉ 4-638 F Cl H CF₃ HH COO^(n)C₅H₁₁ 4-639 F Cl H CF₃ H H COO′⁻C₃H₇ 4-640 F Cl H CF₃ H HCOO^(c)C₅H₉ 4-641 F Cl H CF₃ H H COO^(c)C₆H₁₁ 4-642 F Cl H CF₃ H HCOOCH₂CH═CH₂ 4-643 F Cl H CF₃ H H COOCH₂C≡CH 4-644 F Cl H CF₃ H H CONH₂4-645 F Cl H CF₃ H H CONHCH₃ 4-646 F Cl H CF₃ H H CONHC₂H₅ 4-647 F Cl HCF₃ H H CON(CH₃)₂ 4-648 F Cl H CF₃ H H CON(C₂H₅)₂ 4-649 H Cl H CF₃ H CH₃CH₂Cl 4-650 H Cl H CF₃ H CH₃ CH₂Br 4-651 H Cl H CF₃ H CH₃ CH₂OCH₃ 4-652H Cl H CF₃ H CH₃ CH₂OC₂H₅ 4-653 H Cl H CF₃ H CH₃ CH₂OCH₂OCH₃ 4-654 H ClH CF₃ H CH₃ CH₂OCH₂OC₂H₅ 4-655 H Cl H CF₃ H CH₃ CH₂OCOCH₃ 4-656 H Cl HCF₃ H CH₃ CH₂OCOC₂H₅ 4-657 H Cl H CF₃ H CH₃ CH₂OCO′C₃H₇ 4-658 H Cl H CF₃H CH₃ CH₂OCOCH₂Cl 4-659 H Cl H CF₃ H CH₃ CH₂OCOCCl₃ 4-660 H Cl H CF₃ HCH₃ CH₂OCOCF₃ 4-661 H Cl H CF₃ H CH₃ COOH 4-662 H Cl H CF₃ H CH₃ COOCH₃4-663 H Cl H CF₃ H CH₃ COOC₂H₅ 4-664 H Cl H CF₃ H CH₃ COO^(n)C₃H₇ 4-665H Cl H CF₃ H CH₃ COO^(n)C₄H₉ 4-666 H Cl H CF₃ H CH₃ COO^(n)C₅H₁₁ 4-667 HCl H CF₃ H CH₃ COO′⁻C₃H₇ 4-668 H Cl H CF₃ H CH₃ COO^(c)C₅H₉ 4-669 H Cl HCF₃ H CH₃ COO^(c)C₆H₁₁ 4-670 H Cl H CF₃ H CH₃ COOCH₂CH═CH₂ 4-671 H Cl HCF₃ H CH₃ COOCH₂C≡CH 4-672 H Cl H CF₃ H CH₃ CONH₂ 4-673 H Cl H CF₃ H CH₃CONHCH₃ 4-674 H Cl H CF₃ H CH₃ CONHC₂H₅ 4-675 H Cl H CF₃ H CH₃ CON(CH₃)₂4-676 H Cl H CF₃ H CH₃ CON(C₂H₅)₂ 4-677 F Cl H CF₃ H CH₃ CH₂Cl 4-678 FCl H CF₃ H CH₃ CH₂Br 4-679 F Cl H CF₃ H CH₃ CH₂OCH₃ 4-680 F Cl H CF₃ HCH₃ CH₂OC₂H₅ 4-681 F Cl H CF₃ H CH₃ CH₂OCH₂OCH₃ 4-682 F Cl H CF₃ H CH₃CH₂OCH₂OC₂H₅ 4-683 F Cl H CF₃ H CH₃ CH₂OCOCH₃ 4-684 F Cl H CF₃ H CH₃CH₂OCOC₂H₅ 4-685 F Cl H CF₃ H CH₃ CH₂OCO′C₃H₇ 4-686 F Cl H CF₃ H CH₃CH₂OCOCH₂Cl 4-687 F Cl H CF₃ H CH₃ CH₂OCOCCl₃ 4-688 F Cl H CF₃ H CH₃CH₂OCOCF₃ 4-689 F Cl H CF₃ H CH₃ COOH 4-690 F Cl H CF₃ H CH₃ COOCH₃4-691 F Cl H CF₃ H CH₃ COOC₂H₅ 4-692 F Cl H CF₃ H CH₃ COO^(n)C₃H₇ 4-693F Cl H CF₃ H CH₃ COO^(n)C₄H₉ 4-694 F Cl H CF₃ H CH₃ COO^(n)C₅H₁₁ 4-695 FCl H CF₃ H CH₃ COO′⁻C₃H₇ 4-696 F Cl H CF₃ H CH₃ COO^(c)C₅H₉ 4-697 F Cl HCF₃ H CH₃ COO^(c)C₆H₁₁ 4-698 F Cl H CF₃ H CH₃ COOCH₂CH═CH₂ 4-699 F Cl HCF₃ H CH₃ COOCH₂C≡CH 4-700 F Cl H CF₃ H CH₃ CONH₂ 4-701 F Cl H CF₃ H CH₃CONHCH₃ 4-702 F Cl H CF₃ H CH₃ CONHC₂H₅ 4-703 F Cl H CF₃ H CH₃ CON(CH₃)₂4-704 F Cl H CF₃ H CH₃ CON(C₂H₅)₂ 4-705 H Cl CH₃ CF₃ H H CH₂Cl 4-706 HCl CH₃ CF₃ H H CH₂Br 4-707 H Cl CH₃ CF₃ H H CH₂OCH₃ 4-708 H Cl CH₃ CF₃ HH CH₂OC₂H₅ 4-709 H Cl CH₃ CF₃ H H CH₂OCH₂OCH₃ 4-710 H Cl CH₃ CF₃ H HCH₂OCH₂OC₂H₅ 4-711 H Cl CH₃ CF₃ H H CH₂OCOCH₃ 4-712 H Cl CH₃ CF₃ H HCH₂OCOC₂H₅ 4-713 H Cl CH₃ CF₃ H H CH₂OCO′C₃H₇ 4-714 H Cl CH₃ CF₃ H HCH₂OCOCH₂Cl 4-715 H Cl CH₃ CF₃ H H CH₂OCOCCl₃ 4-716 H Cl CH₃ CF₃ H HCH₂OCOCF₃ 4-717 H Cl CH₃ CF₃ H H COOH 4-718 H Cl CH₃ CF₃ H H COOCH₃4-719 H Cl CH₃ CF₃ H H COOC₂H₅ 4-720 H Cl CH₃ CF₃ H H COO^(n)C₃H₇ 4-721H Cl CH₃ CF₃ H H COO^(n)C₄H₉ 4-722 H Cl CH₃ CF₃ H H COO^(n)C₅H₁₁ 4-723 HCl CH₃ CF₃ H H COO′C₃H₇ 4-724 H Cl CH₃ CF₃ H H COO^(c)H₅H₉ 4-725 H ClCH₃ CF₃ H H COO^(c)H₆H₁₁ 4-726 H Cl CH₃ CF₃ H H COOCH₂CH═CH₂ 4-727 H ClCH₃ CF₃ H H COOCH₂C≡CH 4-728 H Cl CH₃ CF₃ H H CONH₂ 4-729 H Cl CH₃ CF₃ HH CONHCH₃ 4-730 H Cl CH₃ CF₃ H H CONHC₂ ⁻H₅ 4-731 H Cl CH₃ CF₃ H HCON(CH₃)₂ 4-732 H Cl CH₃ CF₃ H H CON(C₂H₅)₂ 4-733 F Cl CH₃ CF₃ H H CH₂Cl4-734 F Cl CH₃ CF₃ H H CH₂Br 4-735 F Cl CH₃ CF₃ H H CH₂OCH₃ 4-736 F ClCH₃ CF₃ H H CH₂OC₂H₅ 4-737 F Cl CH₃ CF₃ H H CH₂OCH₂OCH₃ 4-738 F Cl CH₃CF₃ H H CH₂OCH₂OC₂H₅ 4-739 F Cl CH₃ CF₃ H H CH₂OCOCH₃ 4-740 F Cl CH₃ CF₃H H CH₂OCOC₂H₅ 4-741 F Cl CH₃ CF₃ H H CH₂OCO′C₃H₇ 4-742 F Cl CH₃ CF₃ H HCH₂OCOCH₂Cl 4-743 F Cl CH₃ CF₃ H H CH₂OCOCCl₃ 4-744 F Cl CH₃ CF₃ H HCH₂OCOCF₃ 4-745 F Cl CH₃ CF₃ H H COOH 4-746 F Cl CH₃ CF₃ H H COOCH₃4-747 F Cl CH₃ CF₃ H H COOC₂H₅ 4-748 F Cl CH₃ CF₃ H H COO^(n)C₃H₇ 4-749F Cl CH₃ CF₃ H H COO^(n)C₄H₉ 4-750 F Cl CH₃ CF₃ H H COO^(n)C₅H₁₁ 4-751 FCl CH₃ CF₃ H H COO′C₃H₇ 4-752 F Cl CH₃ CF₃ H H COO^(c)H₅H₉ 4-753 F ClCH₃ CF₃ H H COO^(c)H₆H₁₁ 4-754 F Cl CH₃ CF₃ H H COOCH₂CH═CH₂ 4-755 F ClCH₃ CF₃ H H COOCH₂C≡CH 4-756 F Cl CH₃ CF₃ H H CONH₂ 4-757 F Cl CH₃ CF₃ HH CONHCH₃ 4-758 F Cl CH₃ CF₃ H H CONHC₂ ⁻H₅ 4-759 F Cl CH₃ CF₃ H HCON(CH₃)₂ 4-760 F Cl CH₃ CF₃ H H CON(C₂H₅)₂ 4-761 H Cl CH₃ CF₃ H CH₃CH₂Cl 4-762 H Cl CH₃ CF₃ H CH₃ CH₂Br 4-763 H Cl CH₃ CF₃ H CH₃ CH₂OCH₃4-764 H Cl CH₃ CF₃ H CH₃ CH₂OC₂H₅ 4-765 H Cl CH₃ CF₃ H CH₃ CH₂OCH₂OCH₃4-766 H Cl CH₃ CF₃ H CH₃ CH₂OCH₂OC₂H₅ 4-767 H Cl CH₃ CF₃ H CH₃ CH₂OCOCH₃4-768 H Cl CH₃ CF₃ H CH₃ CH₂OCOC₂H₅ 4-769 H Cl CH₃ CF₃ H CH₃ CH₂OCO′C₃H₇4-770 H Cl CH₃ CF₃ H CH₃ CH₂OCOCH₂Cl 4-771 H Cl CH₃ CF₃ H CH₃ CH₂OCOCCl₃4-772 H Cl CH₃ CF₃ H CH₃ CH₂OCOCF₃ 4-773 H Cl CH₃ CF₃ H CH₃ COOH 4-774 HCl CH₃ CF₃ H CH₃ COOCH₃ 4-775 H Cl CH₃ CF₃ H CH₃ COOC₂H₅ 4-776 H Cl CH₃CF₃ H CH₃ COO^(n−)C₃H₇ 4-777 H Cl CH₃ CF₃ H CH₃ COO^(n)C₄H₉ 4-778 H ClCH₃ CF₃ H CH₃ COO^(n)C₅H₁₁ 4-779 H Cl CH₃ CF₃ H CH₃ COO′C₃H₇ 4-780 H ClCH₃ CF₃ H CH₃ COO^(c)C₅H₉ 4-781 H Cl CH₃ CF₃ H CH₃ COO^(c)C₆H₁₁ 4-782 HCl CH₃ CF₃ H CH₃ COOCH₂CH═CH₂ 4-783 H Cl CH₃ CF₃ H CH₃ COOCH₂C≡CH 4-784H Cl CH₃ CF₃ H CH₃ CONH₂ 4-785 H Cl CH₃ CF₃ H CH₃ CONHCH₃ 4-786 H Cl CH₃CF₃ H CH₃ CONHC₂H₅ 4-787 H Cl CH₃ CF₃ H CH₃ CON(CH₃)₂ 4-788 H Cl CH₃ CF₃H CH₃ CON(C₂H₆)₂ 4-789 F Cl CH₃ CF₃ H CH₃ CH₂Cl 4-790 F Cl CH₃ CF₃ H CH₃CH₂Br 4-791 F Cl CH₃ CF₃ H CH₃ CH₂OCH₃ 4-792 F Cl CH₃ CF₃ H CH₃ CH₂OC₂H₅4-793 F Cl CH₃ CF₃ H CH₃ CH₂OCH₂OCH₃ 4-794 F Cl CH₃ CF₃ H CH₃CH₂OCH₂OC₂H₅ 4-795 F Cl CH₃ CF₃ H CH₃ CH₂OCOCH₃ 4-796 F Cl CH₃ CF₃ H CH₃CH₂OCOC₂H₅ 4-797 F Cl CH₃ CF₃ H CH₃ CH₂OCO′C₃H₇ 4-798 F Cl CH₃ CF₃ H CH₃CH₂OCOCH₂Cl 4-799 F Cl CH₃ CF₃ H CH₃ CH₂OCOCCl₃ 4-800 F Cl CH₃ CF₃ H CH₃CH₂OCOCF₃ 4-801 F Cl CH₃ CF₃ H CH₃ COOH 4-802 F Cl CH₃ CF₃ H CH₃ COOCH₃4-803 F Cl CH₃ CF₃ H CH₃ COOC₂H₅ 4-804 F Cl CH₃ CF₃ H CH₃ COO^(n)C₃H₇4-805 F Cl CH₃ CF₃ H CH₃ COO^(n)C₄H₉ 4-806 F Cl CH₃ CF₃ H CH₃COO^(n)C₅H₁₁ 4-807 F Cl CH₃ CF₃ H CH₃ COO′C₃H₇ 4-808 F Cl CH₃ CF₃ H CH₃COO^(c)C₅H₉ 4-809 F Cl CH₃ CF₃ H CH₃ COO^(c)C₆H₁₁ 4-810 F Cl CH₃ CF₃ HCH₃ COOCH₂CH═CH₂ 4-811 F Cl CH₃ CF₃ H CH₃ COOCH₂C≡CH 4-812 F Cl CH₃ CF₃H CH₃ CONH₂ 4-813 F Cl CH₃ CF₃ H CH₃ CONHCH₃ 4-814 F Cl CH₃ CF₃ H CH₃CONHC₂H₅ 4-815 F Cl CH₃ CF₃ H CH₃ CON(CH₃)₂ 4-816 F Cl CH₃ CF₃ H CH₃CON(C₂H₅)₂ 4-817 H Cl CH₃ CF₃ H H CH₂Cl 4-818 H Cl CH₃ CF₃ H H CH₂Br4-819 H Cl CH₃ CF₃ H H CH₂OCH₃ 4-820 H Cl CH₃ CF₃ H H CH₂OC₂H₅ 4-821 HCl CH₃ CF₃ H H CH₂OCH⁻ ₂OCH₃ 4-822 H Cl CH₃ CF₃ H H CH₂OCH₂OC₂H₅ 4-823 HCl CH₃ CF₃ H H CH₂OCOCH₃ 4-824 H Cl CH₃ CF₃ H H CH₂OCOC₂H₅ 4-825 H ClCH₃ CF₃ H H CH₂OCO′C₃H₇ 4-826 H Cl CH₃ CF₃ H H CH₂OCOCH₂Cl 4-827 H ClCH₃ CF₃ H H CH₂OCOCCl₃ 4-828 H Cl CH₃ CF₃ H H CH₂OCOCF₃ 4-829 H Cl CH₃CF₃ H H COOH 4-830 H Cl CH₃ CF₃ H H COOCH₃ 4-831 H Cl CH₃ CF₃ H HCOOC₂H₅ 4-832 H Cl CH₃ CF₃ H H COO^(n)C₃H₇ 4-833 H Cl CH₃ CF₃ H HCOO^(n)C₄H₉ 4-834 H Cl CH₃ CF₃ H H COO^(n)C₅H₁₁ 4-835 H Cl CH₃ CF₃ H HCOO′C₃H₇ 4-836 H Cl CH₃ CF₃ H H COO^(n)C₅H₉ 4-837 H Cl CH₃ CF₃ H HCOO^(c)C₆H₁₁ 4-838 H Cl CH₃ CF₃ H H COOCH₂CH═CH₂ 4-839 H Cl CH₃ CF₃ H HCOCH₂C≡CH 4-840 H Cl CH₃ CF₃ H H CONH₂ 4-841 H Cl CH₃ CF₃ H H CONHCH₃4-842 H Cl CH₃ CF₃ H H CONHC₂H₅ 4-843 H Cl CH₃ CF₃ H H CON(CH₃)₂ 4-844 HCl CH₃ CF₃ H H CON(C₂ ⁻H₅)₂ 4-845 F Cl CH₃ CF₃ H H CH₂Cl 4-846 F Cl CH₃CF₃ H H CH₂Br 4-847 F Cl CH₃ CF₃ H H CH₂OCH₃ 4-848 F Cl CH₃ CF₃ H HCH₂OC₂H₅ 4-849 F Cl CH₃ CF₃ H H CH₂OCH₂OCH₃ 4-850 F Cl CH₃ CF₃ H HCH₂OCH₂OC₂H₅ 4-851 F Cl CH₃ CF₃ H H CH₂OCOCH₃ 4-852 F Cl CH₃ CF₃ H HCH₂OCOC₂H₅ 4-853 F Cl CH₃ CF₃ H H CH₂OCO′C₃H₇ 4-854 F Cl CH₃ CF₃ H HCH₂OCOCH₂Cl 4-855 F Cl CH₃ CF₃ H H CH₂OCOCCl₃ 4-856 F Cl CH₃ CF₃ H HCH₂OCOCF₃ 4-857 F Cl CH₃ CF₃ H H COOH 4-858 F Cl CH₃ CF₃ H H COOCH₃4-859 F Cl CH₃ CF₃ H H COOC₂H₅ 4-860 F Cl CH₃ CF₃ H H COO^(n)C₃H₇ 4-861F Cl CH₃ CF₃ H H COO^(n)C₄H₉ 4-862 F Cl CH₃ CF₃ H H COO^(n)C₅H₁₁ 4-863 FCl CH₃ CF₃ H H COO′C₃H₇ 4-864 F Cl CH₃ CF₃ H H COO^(c)C₅H₉ 4-865 F ClCH₃ CF₃ H H COO^(c)C₆H₁₁ 4-866 F Cl CH₃ CF₃ H H COOCH₂CH═CH₂ 4-867 F ClCH₃ CF₃ H H COOCH₂C≡CH 4-868 F Cl CH₃ CF₃ H H CONH₂ 4-869 F Cl CH₃ CF₃ HH CONHCH₃ 4-870 F Cl CH₃ CF₃ H H CONHC₂H₅ 4-871 F Cl CH₃ CF₃ H HCON(CH₃)₂ 4-872 F Cl CH₃ CF₃ H H CON(C₂H₅)₂ 4-873 H Cl CH₃ CF₃ H CH₃CH₂Cl 4-874 H Cl CH₃ CF₃ H CH₃ CH₂Br 4-875 H Cl CH₃ CF₃ H CH₃ CH₂OCH₃4-876 H Cl CH₃ CF₃ H CH₃ CH₂OC₂H₅ 4-877 H Cl CH₃ CF₃ H CH₃ CH₂OCH⁻ ₂OCH₃4-878 H Cl CH₃ CF₃ H CH₃ CH₂OCH₂OC₂H₅ 4-879 H Cl CH₃ CF₃ H CH₃ CH₂OCOCH₃4-880 H Cl CH₃ CF₃ H CH₃ CH₂OCOC₂H₅ 4-881 H Cl CH₃ CF₃ H CH₃ CH₂OCO′C₃H₇4-882 H Cl CH₃ CF₃ H CH₃ CH₂OCOCH₂Cl 4-883 H Cl CH₃ CF₃ H CH₃ CH₂OCOCCl₃4-884 H Cl CH₃ CF₃ H CH₃ CH₂OCOCF₃ 4-885 H Cl CH₃ CF₃ H CH₃ COOH 4-886 HCl CH₃ CF₃ H CH₃ COOCH₃ 4-887 H Cl CH₃ CF₃ H CH₃ COOC₂H₅ 4-888 H Cl CH₃CF₃ H CH₃ COO^(n)C₃H₇ 4-889 H Cl CH₃ CF₃ H CH₃ COO^(n)C₄H₉ 4-890 H ClCH₃ CF₃ H CH₃ COO^(n−)C₅H₁₁ 4-891 H Cl CH₃ CF₃ H CH₃ COO′C₃H₇ 4-892 H ClCH₃ CF₃ H CH₃ COO^(c)C₅H₉ 4-893 H Cl CH₃ CF₃ H CH₃ COO^(c)C₆H₁₁ 4-894 HCl CH₃ CF₃ H CH₃ COOCH₂CH═CH₂ 4-895 H Cl CH₃ CF₃ H CH₃ COOCH₂C≡CH 4-896H Cl CH₃ CF₃ H CH₃ CONH₂ 4-897 H Cl CH₃ CF₃ H CH₃ CONHCH₃ 4-898 H Cl CH₃CF₃ H CH₃ CONHC₂H₅ 4-899 H Cl CH₃ CF₃ H CH₃ CON(CH₃)₂ 4-900 H Cl CH₃ CF₃H CH₃ CON(C₂H₅)₂ 4-901 F Cl CH₃ CF₃ H CH₃ CH₂Cl 4-902 F Cl CH₃ CF₃ H CH₃CH₂Br 4-903 F Cl CH₃ CF₃ H CH₃ CH₂OCH₃ 4-904 F Cl CH₃ CF₃ H CH₃ CH₂OC₂H₅4-905 F Cl CH₃ CF₃ H CH₃ CH₂OCH₂OCH₃ 4-906 F Cl CH₃ CF₃ H CH₃CH₂OCH₂OC₂H₅ 4-907 F Cl CH₃ CF₃ H CH₃ CH₂OCOCH₃ 4-908 F Cl CH₃ CF₃ H CH₃CH₂OCOC₂H₅ 4-909 F Cl CH₃ CF₃ H CH₃ CH₂OCO′C₃H₇ 4-910 F Cl CH₃ CF₃ H CH₃CH₂OCOCH₂Cl 4-911 F Cl CH₃ CF₃ H CH₃ CH₂OCOCCl₃ 4-912 F Cl CH₃ CF₃ H CH₃CH₂OCOCF₃ 4-913 F Cl CH₃ CF₃ H CH₃ COOH 4-914 F Cl CH₃ CF₃ H CH₃ COOCH₃4-915 F Cl CH₃ CF₃ H CH₃ COOC₂H₅ 4-916 F Cl CH₃ CF₃ H CH₃ COO^(n)C₃H₇4-917 F Cl CH₃ CF₃ H CH₃ COO^(n)C₄H₉ 4-918 F Cl CH₃ CF₃ H CH₃COO^(n)C₅H₁₁ 4-919 F Cl CH₃ CF₃ H CH₃ COO′C₃H₇ 4-920 F Cl CH₃ CF₃ H CH₃COO^(c)C₅H₉ 4-921 F Cl CH₃ CF₃ H CH₃ COO^(c)C₆H₁₁ 4-922 F Cl CH₃ CF₃ HCH₃ COOCH₂CH═CH₂ 4-923 F Cl CH₃ CF₃ H CH₃ COOCH₂C≡CH 4-924 F Cl CH₃ CF₃H CH₃ CONH₂ 4-925 F Cl CH₃ CF₃ H CH₃ CONHCH₃ 4-926 F Cl CH₃ CF₃ H CH₃CONHC₂H₅ 4-927 F Cl CH₃ CF₃ H CH₃ CON(CH₃)₂ 4-928 F Cl CH₃ CF₃ H CH₃CON(C₂H₅)₂ 4-929 F Cl CH₃ CF₃ H H CH₃ 4-930 F Cl CH₃ CF₃ H H CH₂OH 4-931F Cl CH₃ CF₃ H CH₃ CH₃ 4-932 F Cl CH₃ CF₃ H CH₃ CH₂OH 4-933 H Cl CH₃ CF₃H H CH₃ 4-934 H Cl CH₃ CF₃ H H CH₂OH 4-935 H Cl CH₃ CF₃ H CH₃ CH₃ 4-936H Cl CH₃ CF₃ H CH₃ CH₂OH

[0808] TABLE 5 Compounds of the formula:

Compound No. X R³ R¹ R² R⁵ 5-1  H H CF₂Cl CH₃ CH₃ 5-2  H H CF₂Cl CH₃C₂H₅ 5-3  H H CF₂Cl CH₃ ^(t)C₃H₇ 5-4  H H CF₂Cl CH₃ ^(n)C₃H₇ 5-5  H HCF₂Cl CH₃ ^(t)C₄H₉ 5-6  H H CF₂Cl CH₃ CH₂CH═CH₂ 5-7  H H CF₂Cl CH₃CH(CH₃)CH═CH₂ 5-8  H H CF₂Cl CH₃ CH₂C≡CH 5-9  H H CF₂Cl CH₃ CH(CH₃)C≡CH5-10 F H CF₂Cl CH₃ CH₃ 5-11 F H CF₂Cl CH₃ C₂H₅ 5-12 F H CF₂Cl CH₃^(t)C₃H₇ 5-13 F H CF₂Cl CH₃ ^(n)C₃H₇ 5-14 F H CF₂Cl CH₃ ^(t)C₄H₉ 5-15 FH CF₂Cl CH₃ CH₂CH═CH₂ 5-16 F H CF₂Cl CH₃ CH(CH₃)CH═CH₂ 5-17 F H CF₂ClCH₃ CH₂C≡CH 5-18 F H CF₂Cl CH₃ CH(CH₃)C≡CH 5-19 H H CF₃ CH₃ CH₃ 5-20 H HCF₃ CH₃ C₂H₅ 5-21 H H CF₃ CH₃ ^(t)C₃H₇ 5-22 H H CF₃ CH₃ ^(n)C₃H₇ 5-23 HH CF₃ CH₃ ^(t)C₄H₉ 5-24 H H CF₃ CH₃ CH₂CH═CH₂ 5-25 H H CF₃ CH₃CH(CH₃)CH═CH₂ 5-26 H H CF₃ CH₃ CH₂C≡CH 5-27 H H CF₃ CH₃ CH(CH₃)C≡CH 5-28F H CF₃ CH₃ CH₃ 5-29 F H CF₃ CH₃ C₂H₅ 5-30 F H CF₃ CH₃ ^(n)C₃H₇ 5-31 F HCF₃ CH₃ ^(t)C₄H₉ 5-32 F H CF₃ CH₃ CH₂CH≡CH₂ 5-33 F H CF₃ CH₃CH(CH₃)CH═CH₂ 5-34 F H CF₃ CH₃ CH₂H₅ 5-35 F H CF₃ CH₃ CH(CH₃)C≡CH 5-36 HH CF₂Cl H CH₃ 5-37 H H CF₂Cl H C₂H₅ 5-38 H H CF₂Cl H ^(t)C₃H₇ 5-39 H HCF₂Cl H ^(n)C₃H₇ 5-40 H H CF₂Cl H ^(t)C₄H₉ 5-41 H H CF₂Cl H CH₂CH═CH₂5-42 H H CF₂Cl H CH(CH₃)CH═CH₂ 5-43 H H CF₂Cl H CH₂C≡CH 5-44 H H CF₂Cl HCH(CH₃)C≡CH 5-45 F H CF₂Cl H CH₃ 5-46 F H CF₂Cl H C₂H₅ 5-47 F H CF₂Cl H^(t)C₃H₇ 5-48 F H CF₂Cl H ^(n)C₃H₇ 5-49 F H CF₂Cl H ^(t)C₄H₉ 5-50 F HCF₂Cl H CH₂CH≡CH₂ 5-51 F H CF₂Cl H CH(CH₃)CH═CH₂ 5-52 F H CF₂Cl HCH₂C≡CH 5-53 F H CF₂Cl H CH(CH₃)C≡CH 5-54 H H CF₃ H CH₃ 5-55 H H CF₃ HC₂H₅ 5-56 H H CF₃ H ^(t)C₃H₇ 5-57 H H CF₃ H ^(n)C₃H₇ 5-58 H H CF₃ H^(t)C₄H₉ 5-59 H H CF₃ H CH₂CH═CH₂ 5-60 H H CF₃ H CH(CH₃)CH═CH₂ 5-61 H HCF₃ H CH₂C≡CH 5-62 H H CF₃ H CH(CH₃)C≡CH 5-63 F H CF₃ H CH₃ 5-64 F H CF₃H C₂H₅ 5-65 F H CF₃ H ^(t)C₃H₇ 5-66 F H CF₃ H ^(n)C₄H₉ 5-67 F H CF₃ HCH₂CH═CH₂ 5-68 F H CF₃ H CH(CH₃)CH═CH₂ 5-69 F H CF₃ H CH₂C⁻≡CH 5-70 F HCF₃ H CH(CH₃)C≡CH 5-71 H CH₃ CF₃ H CH₃ 5-72 H CH₃ CF₃ H C₂H₅ 5-73 H CH₃CF₃ H ^(t)C₃H₇ 5-74 H CH₃ CF₃ H ^(n)C₃H₇ 575 H CH₃ CF₃ H ^(t)C₄H₉ 5-76 HCH₃ CF₃ H CH₂CH═CH₂ 5-77 H CH₃ CF₃ H CH(CH₃)CH═CH 5-78 H CH₃ CF₃ HCH₂C≡CH 5-79 H CH₃ CF₃ H CH(CH₃)C≡CH 5-80 F CH₃ CF₃ H CH₃ 5-81 F CH₃ CF₃H C₂H₅ 5-82 F CH₃ CF₃ H ^(t)C₃H₇ 5-83 F CH₃ CF₃ H ^(t)C₄H₉ 5-84 F CH₃CF₃ H CH₂CH═CH₂ 5-85 F CH₃ CF₃ H CH(CH₃)CH═CH₂ 5-86 F CH₃ CF₃ H CH₂C≡CH5-87 F CH₃ CF₃ H CH(CH₃)C≡CH

[0809] The physical properties (melting point, m.p.) or ¹H-NMR (250 or300 MHz, CDCl₃, TMS, δ (ppm)) data for some of the present compounds areshown below.

[0810] Compound 1-332, m.p. 97.0° C.

[0811] Compound 1-335, m.p. 80.8° C.

[0812] Compound 1-337, m.p. 91.5° C.

[0813] Compound 1-338, m.p. 86.1° C.

[0814] Compound 1-344, m.p. 94.2° C.

[0815] Compound 1-347, m.p. 80.7° C.

[0816] Compound 1-350, 2.41 (3H, q, J=1.8 Hz), 4.05-4.35 (2H, b),6.87-6.94 (1H, m), 7.03 (1H, d, J=2.4 Hz), 7.33 (1H, d, J=8.5 Hz), 7.98(1H, s) Compound 1-353,m.p. 124.0° C.

[0817] Compound 1-367, 2.44 (3H, q, J=1.9 Hz), 3.04 (3H, s), 6.88 (1H,s), 7.37 (1H, d, J=9.0 Hz), 7.79 (1H, d, J=7.0 Hz), 8.01 (1H, s)

[0818] Compound 1-369, 2.44 (3H, q, J=2.0 Hz), 4.57 (2H, s), 7 06 (1H,s), 7 38 (1H, d, J=9.0 Hz), 7.83 (1H, d, J=6.9 Hz), 8.01 (1H, s)

[0819] Compound 1-391, m.p. 177.6° C.

[0820] Compound 1-392, m.p. 172.5° C.

[0821] Compound 1-398, m.p. 133.1° C.

[0822] Compound 1-420, 1.25 (3H, t, J=7.5 Hz), 1.51 (3H, d. J=7.0 Hz),2.42 (3H, q, J=18 Hz), 4.0-4.18 (3H, m), 4 82 (1H, d, J=7.9 Hz), 6.59(1H, d, J=6 3 Hz), 7 23 (1H, d, J=93 Hz), 7 97 (1H, s)

[0823] Compound 1-429, 1 40 (6H, d, J=63 Hz), 2 43 (3H, q, J=2.4 Hz), 452-4 63 (1H, m), 7.14 (05H. d. J=24 Hz), 7 17 (0.5H, d. J=2.4 Hz). 7 24(1H d. J=36 Hz). 7.29 (1H, s). 7 46 (11H, d, J=8.4 Hz)

[0824] Compound 1-439, In p 110 6° C.

[0825] Compound 1-449, 1 29 (311, t, J=75 Hz), 2.42 (3H, q, J=24 Hz), 428 (21H q. J 7.5 Hz). 4.73 (2H, s). 7.20-7.32 (2H, in), 7.49 (1H, d,J=10.4 Hz), 8.00 (1H, s)

[0826] Compound 1-456, 1.70 (3H, d, J=6.9 Hz), 2.41 (3H, q, J=2.1 Hz),3.77 (3H, s), 4.81 (1H, q, J=6.9 Hz), 7.21-7.28 (2H, m), 7.47 (1H, d,J=8.7 Hz), 7.99 (1H, s)

[0827] Compound 1-474, m.p. 110.6° C.

[0828] Compound 1-475, 1.46 (3H, t, J=5.8 Hz), 2.44 (3H, q, J=1.5 Hz),4.07 (2H, q, J=5.8 Hz), 6.94 (1H, d, J=5.0 Hz), 7.29 (1H, d, J=7.5 Hz),8.01 (1H, s)

[0829] Compound 1-476, 1.38 (6H, d, J=6.3 Hz), 2.43 (3H, q, J=2.0 Hz),4.47 (1H, m), 6.99 (1H, d, J=5.0 Hz), 7.29 (1H, d, J=9.5 Hz), 8.00 (1H,s)

[0830] Compound 1-482, m.p. 79.8° C.

[0831] Compound 1-483, m.p. 132.7° C.

[0832] Compound 1-486, m.p. 140.7° C. (decomp.)

[0833] Compound 1-487, m.p. 114.1° C.

[0834] Compound 1-491, m.p. 82.9° C.

[0835] Compound 1-495, m.p. 80.4° C.

[0836] Compound 1-496, m.p. 102.0° C.

[0837] Compound 1-497, m p. 82.9° C.

[0838] Compound 1-498, m.p. 75.6° C.

[0839] Compound 1-499, 0.88 (3H, t, J=7 Hz), 1.2-1.4 (4H, m), 1.55-1.70(2H, m), 2.43 (3H, q, J=2 Hz), 4.19 (2H, t, J=7 Hz), 4.68 (2H, s), 6.98(1H, d, J=7 Hz).7 33 (1H, d J=8 Hz), 7.99 (1H, s)

[0840] Compound 1-500, 1 26 (6H, d, J=6.3 Hz), 2 43 (3H, q, J=2 Hz),4.65 (2H, s), δ 05-5.18 (1H, m), 6.98 (1H, d, J=7 Hz), 7.33 (1H, d, J=8Hz), 7.98 (1H, s)

[0841] Compound 1-501, 1.5-1.9 (8H, m). 2 43 (3H, q, J=2 Hz),4 65 (2H,s), δ 2-5 4(1H, m), 6.97 (1H, d, J=7 Hz), 7.33 (1H, d, J=8 Hz), 7.98(11H, s)

[0842] Compound 1-503, 1 68 (3H, d. J=7 Hz), 2 43 (3H, q, J=2 Hz), 3 76(31H. s). 4.73 (11H, q. J=7 Hz), 6.98 (1H, d, J=7 Hz), 7.32 (1H, d, =8Hz), 7.99

[0843] Compound 1-504, 1.25 (3H, t, J=7.3 Hz), 1.68 (3H, d, J=6.8 Hz),2.42 (3H, q, J=2.0 Hz), 4.21 (2H, q, J=7.3 Hz), 4.70 (1H, q, J=6.8 Hz),6.99 (1H, d, J=6.8 Hz). 7.32 (1H, d, J=9.3 Hz), 7.98 (1H, s)

[0844] Compound 1-511, m.p. 110.7° C.

[0845] Compound 1-518, m.p. 131.2° C. (decomp.)

[0846] Compound 1-576, 2.43 (3H, q, J=1.8 Hz), 3.67 (2H, s), 3.72 (3H,s), 7.32 (1H, d, J=8.5 Hz), 7.59 (1H, d, J=7.1 Hz), 8.2 (1H, s)

[0847] Compound 1-577, 1.15 (3H, t,J=7.5 Hz), 2.36 (3H, q, J=1.8 Hz),3.58 (2H, s), 4.09 (2H, q, J=7.5 Hz), 7.28 (1H, d, J=8.6 Hz), 7.52 (1H,d, J=7.1 Hz), 7.93 (1H, s)

[0848] Compound 1-579, m.p. 71.6° C.

[0849] Compound 1-581, m.p. 97.5° C.

[0850] Compound 1-584, 1.53 (3H, d, J=7.2 Hz), 2.43 (3H, q, J=1.8 Hz),3.66 (3H, s), 3.88 (1H, q, J=7.2 Hz), 7.38 (1H, d, J=9.6 Hz), 7.66 (1H,d, J=7.5 Hz), 7.99 (1H, s)

[0851] Compound 1-585, 1.17 (3H, t, J=6.9 Hz), 1.53 (3H, d, J=7.2 Hz),2.43 (3H, q, J=1.8 Hz), 3.89 (1H, q, J=7.2 Hz), 4.11 (2H, q, J=6.9 Hz),7.37 (1H, d, J=9.6 Hz). 7.67 (1H, d, J=9.0 Hz), 7.99 (1H, s)

[0852] Compound 1-586,0.85 (3H, t, J=6.8 Hz), 1.51-1.62 (5H, m), 2.43(3H, q, J=1.8 Hz), 3.89 (1H, q, J=72 Hz), 4.02 (2H, t, J=6.8 Hz), 7.33(1H, d, J=9.5 Hz). 7.66 (1H, d, J=75 Hz),7 98 (1H, s)

[0853] Compound 1-587, 0 88 (3H, t, J=7.2 Hz), 1.30-1.40 (2H, m),1.47-1.55 (5H, m),2 43 (3H, q, J=1.8 Hz), 3.89 (1H, q, J=71 Hz),4.02-4.08 (2H, m), 7.36 (1H, d, J=94 Hz),7 66 (1H, d, J=7.5 Hz), 7.99(1H, s)

[0854] Compound 1-619, 2.45 (3H, q, =16 Hz), 7.60 (1H, d, J=8.6 Hz), 780-7 86 (1H, m), 8.04(1H, s). 8.36(1H, d, J=25 Hz)

[0855] Compound 1-621, 1.40(3H, t, J=7.1 Hz), 2.43 (3H, q, J=1.8 Hz),4.41 (2H. q. J=7.1 Hz). 7.56 (11H. d. J=8.6 Hz), 7.72-7.78 (1H. i),8.02(1H, s), 8.16 (1H, d, J=2.7 Hz)

[0856] Compound 1-625, 1.39 (6H, d, J=6.2 Hz), 2.43 (3H, q, J=1.6 Hz),5.23-5.28 (1H, m), 7.54 (1H, d, J=8.7 Hz), 7.70-7.76 (1H, m), 8.02 (1H,s), 8.10 (1H, d, J=2.6 Hz)

[0857] Compound 1-632, m.p. 76.1° C.

[0858] Compound 1-637, m.p. 102.8° C.

[0859] Compound 1-641, 2.43 (3H, q, J=2.0 Hz), 3.92 (3H, s), 7.39 (1H,d, J=9.5 Hz), 8.02 (1H, s), 8.07 (1H, d, J=7.7 Hz)

[0860] Compound 1-642, 1.39 (3H, t, l=7.2 Hz), 2.44 (3H, q, J=1.9 Hz),4.40 (2H, q, J=7.2 Hz), 7.38 (1H, d, J=9.5 Hz), 8.00-8.06 (2H, m)

[0861] Compound 1-981, m.p. 87.1° C.

[0862] Compound 1-987, 4.0-4.4 (2H, b), 6.8-6.9 (1H, m), 7.04 (1H, d,J=2.4 Hz), 7.28 (1H, q, J=1.2 Hz), 7.35 (1H, d, J=8.6 Hz), 8.02 (1H, d,J=2.2 Hz)

[0863] Compound 1-1025, 5.92 (1H, s), 7.16 (0.5H, d, J=2.4 Hz), 7.19(0.5H, d, J=2.4 Hz), 7.30 (1H, q, J=1.1 Hz), 7.34 (1H, d,J=5.7 Hz), 7.43(1H, d, J=9.0 Hz), 8.04 (1H, q, J=3.0 Hz)

[0864] Compound 1-1028, m.p. 180.2° C., 5.65-5.9 (1H, br), 7.09 (1H, d,J=7 Hz), 7.27-7.30 (2H, m), 8. 10 (1H, q, J=2.2 Hz)

[0865] Compound 1-1029, 7.09 (1H, d, J=6.4 Hz), 7.31 (1H, q, J=1 1 Hz),7 42 (1H, d, J=8.8 Hz), δ 04 (1H, q, J=2.2 Hz)

[0866] Compound 1-1035, m.p. 61.1° C.

[0867] Compound 1-1057, m p. 158° C.

[0868] Compound 1-1066, m.p. 89.1° C.

[0869] Compound 1-1076, m p 113.5° C.

[0870] Compound 1-1086, m.p 83.9° C.

[0871] Compound 1-1093, m.p. 83.1° C.

[0872] Compound 1-1113, m.p. 68.6° C.

[0873] Compound 1-1123, m.p. 147.4° C.

[0874] Compound 1-1124, m.p. 117.2° C.

[0875] Compound 1-1133, m.p. 149.2° C. (decomp.)

[0876] Compound 1-1140, m.p. 99.1° C.

[0877] Compound 1-1141, m.p. 80.2° C.

[0878] Compound 1-1213, m.p. 85.8° C.

[0879] Compound 1-1214, m.p. 65.1° C.

[0880] Compound 1-1221, 1.54 (3H, d, J=7.2 Hz), 3.66 (3H, s), 3.90 (1H,q, J=7.2 Hz), 7.31 (1H, s), 7.39 (1H, d, J=9.0 Hz), 7.67 (1H, d, J=8.7Hz), 8.04 (1H, d, J=3.6 Hz)

[0881] Compound 1-1222, 1.16 (3H, t, J=5.1 Hz), 1.53 (3H, d, J=7.2 Hz),3.89 (1H, q, J=7.2 Hz), 4.10 (2H, q, J=5.1 Hz), 7.30 (1H, q, J=1.1 Hz),7.38 (1H, d, J=9.0 Hz), 7.68 (1H, d, J=7.5 Hz), 8.04 (1H, q, J=2.2 Hz)

[0882] Compound 1-1226, 1.12 (3H, d, J=6.0 Hz), 1.21 (3H, d, J=6.0 Hz),1.52 (3H, d, J=3.0 Hz), 3.88 (1H, q, J=3.0 Hz), 4.85-5.03 (1H, m), 7.30(1H, q, J=1.8 Hz). 7.37 (1H, d, J=9.0 Hz), 7.67 (1H, d, J=7.5 Hz), 8.02(1H, q, J=2 1 Hz)

[0883] Compound 1-1256, 7.35 (1H, q, J=1.1 Hz), 7.62 (1H, d, J=8.7 Hz),7.82-7.88 (1H, m), 8.09 (1H, d, J=2.2 Hz), 8.35 (1H, d, J=2.6 Hz)

[0884] Compound 1-1258, 1.41 (3H, t, J=7.1 Hz), 4.42 (2H, q, J=7.1 Hz),7 31 (1H, s), 7.57 (1H, d, 3=87 Hz), 7.74-7.79 (1H, m), 8.07 (1H, q,J=21 Hz). 8 16 (1H, d, J=2.6 Hz)

[0885] Compound 1-1269 in p. 89.7° C.

[0886] Compound 1-1274, m.p 154.2° C.

[0887] Compound 1-1278, m.p 128.6° C.

[0888] Compound 1-1279, 1 40 (3H, t, J=7.1 Hz), 4.40 (2H, q, J=7.1 Hz),7.33 (1H, q, J=1.1 Hz), 7.39 (1H, d, J=9.4 Hz), 8.05 (1H, d, J=8.3 Hz),8.07 (1H, s)

[0889] Compound 1-1346, 2.48 (31H, s), 5.66 (1H, s), 7.08 (1H, d, J=7.8Hz), 7.28 (1H, d, J=9.0 Hz), 7.32(11H, s)

[0890] Compound 1-1431, m.p. 74.5° C.

[0891] Compound 1-1441, m.p. 128.2° C.

[0892] Compound 1-1442, 1.73 (3H, d, J=6.6 Hz), 2.49 (3H, q,J=1.3 Hz),2.54 (1H, d, J=2.0 Hz), 4.84 (1H, m), 7.22 (1H, d, J=6.5 Hz), 7.28-7.34(2H, m)

[0893] Compound 1-1451, 1.29 (3H, t, J=7.0 Hz), 2.47 (3H, q, J=1.4 Hz),4.27 (2H, q, J=7.0 Hz), 4.68 (2H, s), 6.99 (1H, d, J=7.1 Hz), 7.32 (1H,s), 7.34 (1H, d, J=7.2 Hz)

[0894] Compound 1-1458, 1.69 (3H, d, J=6.8 Hz), 2.48 (3H, q, J=1.3 Hz),3.76 (3H, s), 4.74 (1H, q, J=6.8 Hz), 7.01 (1H, d, J=6.5 Hz),7.29-7.34(2H, m)

[0895] Compound 1-1540, 1.17 (3H, t,J=7.0 Hz), 1.54 (3H, d, J=7.3 Hz),2.48 (3H, q, J=1.4 Hz), 3.89 (1H, q, J=7.3 Hz), 4.11 (2H, q, J=7.0 Hz),7.31 (1H, s), 7.37 (11H, d, J=9.5 Hz), 7.67(1H, d, J=7.5 Hz)

[0896] Compound 1-1617, m.p. 105.7° C.

[0897] Compound 1-1622, 1.27 (3H, t, J=7.0 Hz), 2.42 (3H, q, J=2.0 Hz),3.26 (0.3H, d, J=7.6 Hz), 3.32 (0.7H, d, J=7.6 Hz), 3.49 (0.7H, d, J=7.6Hz), 3 54 (0.3H, d, J=7.6 Hz), 4.23 (2H, q, J=7.0 Hz), 4.54 (0.5H, d,J=7.6 Hz), 4.57 (0.5H, d. J=7.6 Hz), 7.34 (1H, d, J=9.3 Hz), 7.40(1H, d,J=7.5 Hz), 8.00 (1H, s)

[0898] Compound 1-1627, m p 182.2° C.

[0899] Compound 1-1638, 3.66 (2H, s). 7 31 (1H, s), 7.34 (1H, d, J=93Hz), 7 62 (1H, d. J=72 Hz),8 08 (1H, s)

[0900] Compound 1-1639, m p 158.9° C. (decomp.)

[0901] Compound 1-1641, 1.55 (3H, d, J=7.2 Hz), 3 88 (H, q, J=72 Hz), 732 (1H, s), 7 37 (1H, d, J=92 Hz), 7.69 (1H, d, J=7.1 Hz), 8.03 (1H, s)

[0902] Compound 1-1650, 1.11 (3H, t, J=7.5 Hz), 2.03-2.12(2H, m),2.43(3H, q, J=1.8 Hz), 3.75 (3H, s), 4.58 (1H, t, J=7.5 Hz), 6.92 (1H,d, J=8.2 Hz),7.32 (1H, d, J=9.3 Hz), 8.00 (1H, s)

[0903] Compound 1-1655, m.p. 119.7° C., 1.29 (3H, t, J=7.1 Hz), 2.43(3H, q, J=1.8 Hz), 4.26 (2H, q, J=7.1 Hz), 4.68 (2H, s), 6.91 (1H, s),7.60 (1H, s), 7.99 (1H, s)

[0904] Compound 1-1663, m.p. 136.2° C., 2.44 (3H, q, J=1.8 Hz), 2.58(1H, t, J=2.3 Hz), 4.78 (2H, d, J=2.3 Hz), 7.12 (1H, s), 7.59 (1H, s),8.01 (1H, s)

[0905] Compound 1-1665, 1.23 (3H, t, J=6.9 Hz), 1.68 (3H, d, J=6.8 Hz),2.42 (3H, q, J=1.8 Hz), 4.1-4.3 (2H, m), 4.72 (1H, q, J=6.8 Hz), 6.90(1H, s), 7.58 (1H, s), 7.97 (1H, s)

[0906] Compound 1-1670, m.p. 118.1° C.

[0907] Compound 1-1673, m.p. 107.2° C.

[0908] Compound 1-1678, m.p. 164.7° C.

[0909] Compound 1-1679, 1.73 (3H, d, J=6.9 Hz), 2.54 (1H, d, J=2.1 Hz),4.73-4.90 (1H, m), 7.20 (1H, d, J=6.3 Hz), 7.30 (1H, s), 7.49 (1H, d,J=8.7 Hz), 8.00 (1H, s)

[0910] Compound 1-1680, m.p. 90.1° C.

[0911] Compound 1-1681, m.p. 148.1° C.

[0912] Compound 1-1682, m.p. 107.0° C.

[0913] Compound 1-1683, 1.25 (3H, t, J=72 Hz), 1.68 (3H, d, J=6.8 Hz),2.42 (3H, q, J=1.5 Hz), 4.13-4.26 (2H, m), 4.70 (1H, q, J=6.8 Hz), 6.96(1H, d, J=6.3 Hz). 7.48 (1H, d, J=9.0 Hz), 7.97 (1H, s)

[0914] Compound 1-1687, m p. 200.1° C.

[0915] Compound 1-1689, m p. 76.3° C.

[0916] Compound 1-1690, m p. 196.1° C.

[0917] Compound 1-1691, 3 06 (3H, s). 7 10-7.30 (1H, b), 7 30 (1H, s), 764 (1H, s), 7.74 (1H, s), 8.06 (1H, q, J=2.1 Hz)

[0918] Compound 1-1701, 1.39 (3H, t, J=7.1 Hz), 4.40 (2H, q, J=7.1 Hz),7.33(11H, q, J=1.1 Hz), 7.69 (1H, s), 7.97(1H, s), 8.06 (1H, q, J=2.2Hz)

[0919] Compound 1-1718, m.p. 63.9° C.

[0920] Compound 1-1719, m.p. 189.5° C.

[0921] Compound 1-1720, m.p. 117.3° C.

[0922] Compound 1-1721, m.p. 156.1° C.

[0923] Compound 1-1722, 2.47 (3H, q, J=1.8 Hz), 3.05 (3H, s), 7.15-7.30(1H, b), 7.66 (1H, s), 7.78 (1H, s), 8.03 (1H, s)

[0924] Compound 1-1732, 1.38 (3H, t, J=7.1 Hz), 2.44 (3H, q, J=1.8 Hz),4.39 (2H, q, J=7.1 Hz), 7.68 (1H, s), 7.96 (1H, s), 8.02 (1H, s)

[0925] Compound 1-1748, 1.38 (6H, d, J=6.0 Hz), 2.44 (3H, q, J=1.9 Hz),4.40-4.59 (1H, m), 6.95 (1H, s), 7.55 (1H, s), 8.00 (1H, s)

[0926] Compound 1-1780, m.p. 76.4° C.

[0927] Compound 1-1781, 3.51 (3H, s), 3.51 (3H, s), 7.30 (1H, q, J=1.2Hz), 7.59 (1H, d, J=6.7 Hz), 7.65 (1H, d, J=9.0 Hz), 8.06 (1H, d, J=2.1Hz)

[0928] Compound 1-1782, 3.03 (3H, s), 7.09 (1H, s), 7.32 (1H, q, J=1.0Hz), 7.53 (1H, d, J=8.7 Hz), 7.77 (1H, d, J=6.8 Hz), 8.07 (1H, q, J=2.2Hz)

[0929] Compound 1-1783, 1.38 (6H, d, J=6.1 Hz), 2.43 (3H, q, J=1.7 Hz),4.4-4.6(1H, m), 6.95 (1H, d, J=6.4 Hz), 7.47 (1H, d, J=8.9 Hz), 8.00(1H, s)

[0930] Compound 1-1785, 2.43 (3H, q, J=1.9 Hz), 3.03 (3H, s), 7.03 (1H,s), 7 52 (1H, d, J=8.8 Hz), 7.76(1H, d, J=6.9 Hz), 8.02 (1H, s)

[0931] Compound 1-1789, m.p. 78.3° C.

[0932] Compound 1-1790, m.p. 63.2° C.

[0933] Compound 1-1879, 2.42 (3H, q, J=1.8 Hz), δ 38 (2H, s), 7 28-7 47(5H, m). 7 56 (1H, d, J=8.7 Hz), 7 72-7.79 (1H, m), 8.00 (1H, s), 8 18(1H, d, J=2 5 Hz)

[0934] Compound 1-1881, 2 20 (0.75H, s), 2 24 (2 25H, s), 2.42 (3H, q, J1 9 Hz), 3.82 (0.75H, s), 3.98 (2.25H, s). 7.47-7.68 (3H, m), 8.00 (1H,s)

[0935] Compound 1-1901, m.p. 99.2° C.

[0936] Compound 1-1908, m.p. 77.6° C.

[0937] Compound 1-1910, m.p. 75.3° C.

[0938] Compound 1-1930, m.p. 139.7° C.

[0939] Compound 1-2051, 1.25 (3H, t, J=7.2 Hz), 2.42 (3H, q, J=1.9 Hz),4.17 (2H, q, J=7.2 Hz), 4.71 (2H, s), 4.82 (2H, s), 7.10 (1H, d, J=6.3Hz), 7.33 (1H, d, J=9.1 Hz), 7.99 (1H, s)

[0940] Compound 1-2054, 1.24 (3H, t, J=7.1 Hz), 1.51 (3H, d, J=7.2 Hz),2.42 (3H, q, J=1.8 Hz), 4.15 (2H, q, J=7.1 Hz), 4.78 (2H, s), 5.19 (1H,q, J=7.2 Hz), 7.08 (1H, d, J=6.3 Hz), 7.32 (1H, d, J=9.1 Hz), 7.98 (1H,s)

[0941] Compound 2-203, 2.3-2.4 (1H, m), 2.35 (3H, q, J=1.9 Hz), 4.5-4.7(4H, m), 7.00 (1H, d, J=6.5 Hz), 7.19 (1H, m), 7.39 (1H, d, J=2.5 Hz),7.95 (1H, s)

[0942] Compound 2-251, m.p. 168.3° C.

[0943] Compound 2-328, 0.90 (3H, t, J=7.3 Hz), 1.54 (3H, d, J=7.0 Hz),1.70-1.90 (2H, m), 2.46 (3H, m), 4.50 (1H, m), 7.18 (1H, d, J=5.75 Hz),7.35 (1H, d, J=8.8 Hz), 8.04 (1H, s)

[0944] Compound 2-583, m.p. 149.1° C.

[0945] Compound 2-631, m.p. 168.3° C.

[0946] Compound 2-708, 0.90 (3H, t, J=7.3 Hz), 1.55 (3H, d, J=7.0 Hz),1.75-1.95 (2H, m), 4.50 (1H, m), 7.22 (1H, d, J=5.8 Hz), 7.30-7.40 (2H,m), 8.08 (1H, q, J 22 Hz)

[0947] Compound 2-821, m.p. 162.7° C.

[0948] Compound 3-139, m p. 88.2° C.

[0949] Compound 4-434, 1 67 (3H, s), 2.35 (3H, q, J=1.7 Hz), 3.0-3.2(1H, m), 3 4-37 (1H, m), 3.71 (3H, s),7 03 (1H, d, J=50 Hz), 7.97 (1H,q, J=3.3 Hz)

[0950] Compound 4-451, 1.53 (6H, s), 2.43 (3H, q, J=19 Hz), 2.96 (1H, d,J=16 2 Hz), 3.08(1H, d, J=16.2 Hz), 7.07(1H, d, J=9.9 Hz), 7,99(11H, s)

[0951] Compound 4-452, 14-1.5 (3H, m), 2.43 (3H, q, J=2.0 Hz), 2.7-3.0(11H, i). 3.1-3.5 (11H m), 35-3.8 (H in), 7.07 (111 d, J=10.0 Hz), 8.00(11H, q, J=2.5 Hz)

[0952] The following will describe formulation examples, in which thepresent compounds are designated by their compound numbers shown inTables 1 to 5 and parts are by weight.

FORMULATION EXAMPLE 1

[0953] Fifty parts of each of compounds 1-1 to 1-2157, 2-1 to 2-950, 3-1to 3-582, 4-1 to 4-936, and 5-1 to 5-87, 3 parts of calciumligninsulfonate, 2 parts of sodium laurylsulfate, and 45 parts ofsynthetic hydrated silicon oxide are well pulverized and mixed to give awettable powder for each compound.

FORMULATION EXAMPLE 2

[0954] Ten parts of each of compounds 1-1 to 1-2157, 2-1 to 2-950, 3-1to 3-582, 4-1 to 4-936, and 5-1 to 5-87, 14 parts of polyoxyethylenestyryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 35parts of xylene, and 35 parts of cyclohexanone are well mixed to give anemulsifiable concentrate for each compound.

FORMULATION EXAMPLE 3

[0955] Two parts of each of compounds 1-1 to 1-2157, 2-1 to 2-950, 3-1to 3-582, 4-1 to 4-936, and 5-1 to 5-87, 2 parts of synthetic hydratedsilicon oxide, 2 parts of calcium ligninsulfonate, 30 parts ofbentonite, and 64 parts of kaoline clay are well pulverized and mixed,to which water is added, and the mixture is well kneaded, granulated,and dried to give a granule for each compound.

FORMULATION EXAMPLE 4

[0956] Twenty-five parts of each of compounds 1-1 to 1-2157, 2-1 to2-950, 3-1 to 3-582, 4-1 to 4-936, and 5-1 to 5-87, 50 parts of 10%aqueous polyvinyl alcohol solution, and 25 parts of water are mixed, andthe mixture is pulverized until the average particle size becomes 5 μmor less to give a flowable for each compound.

FORMULATION EXAMPLE 5

[0957] Five parts of compound 1-1650 is added to 40 parts of 10% aqueouspolyvinyl alcohol solution and dispersed by emulsion with a homogenizeruntil the mean particle size becomes 10 μm or less, to which 55 parts ofwater is added to give a concentrated emulsion.

[0958] The following test examples will demonstrate that the presentcompounds are useful as active ingredients of herbicides. The presentcompounds are designated by their compound numbers shown in Tables 1 to5.

[0959] The herbicidal activity and phytotoxicity were evaluated at 6levels with indices of 0 to 5, i.e., designated by the numeral “0”, “1”,“2”, “3”, “4” or “5”, wherein “0” means that there was no or littledifference in the degree of germination or growth between the treatedand the untreated test plants at the time of examination, and “5” meansthat the test plants died complete or their germination or growth wascompletely inhibited. The herbicidal activity is excellent when rated at“4” or “5” but insufficient when rated at “3” or lower. Thephytotoxicity is no problematic on practical use when rated at “0” or“1” but not allowed when rated at “2” or higher.

TEST EXAMPLE 1 Foliar Treatment on Upland Fields

[0960] Cylindrical plastic pots of 10 cm in diameter and 10 cm in depthwere filled with soil, in which the seeds of entireleaf morningglory(Ipomoea hederacea var. integriuscula) and velvetleaf (Abutilontheophrasti) were sowed, and the test plants were grown in a greenhousefor 19 days. Each of the test compounds listed below was formulated intoan emulsifiable concentrate according to Formulation Example 2, whichwas diluted with water containing a spreading agent to a prescribedconcentration. The dilution was uniformly sprayed over the foliage ofthe test plants with a sprayer at a volume of 1000 liters per hectareAfter the application, the test plants were grown in the greenhouse for19 days, and the herbicidal activity was examined. The results are shownin Table 6 TABLE 6 Application amount of Herbicidal activity Test activeingredient Entireleaf compound (g/ha) morningglory Velvetleaf 1-332  5005 5 1-335  500 5 5 1-338  500 5 5 1-347  500 5 5 1-350  500 5 5 1-353 500 5 5 1-367  500 5 5 1-369  500 5 5 1-391  500 5 5 1-392  500 5 51-398  500 5 5 1-420  500 5 5 1-429  500 5 5 1-439  500 5 5 1-449  500 55 1-456  500 5 5 1-474  500 5 5 1-475  500 5 5 1-476  500 5 5 1-482  5005 5 1-483  500 5 5 1-486  500 5 5 1-487  500 5 5 1-491  500 5 5 1-495 500 5 5 1-496  500 5 5 1-497  500 5 5 1-498  500 5 5 1-499  500 5 51-500  500 5 5 1-501  500 5 5 1-503  500 5 5 1-504  500 5 5 1-511  500 55 1-576  500 5 5 1-577  500 5 5 1-579  500 5 5 1-581  500 5 5 1-584  5005 5 1-585  500 5 5 1-586  500 5 5 1-587  500 5 5 1-619  500 5 5 1-621 500 5 5 1-625  500 5 5 1-637  500 5 5 1-641  500 5 5 1-642  500 5 51-987  500 5 5 1-1025 500 5 5 1-1028 500 5 5 1-1029 500 5 5 1-1035 500 55 1-1057 500 5 5 1-1066 500 5 5 1-1076 500 5 5 1-1086 500 5 5 1-1093 5005 5 1-1113 500 5 5 1-1123 500 5 5 1-1124 500 5 5 1-1133 500 5 5 1-1140500 5 5 1-1141 500 5 5 1-1213 500 5 5 1-1214 500 5 5 1-1221 500 5 51-1222 500 5 5 1-1226 500 5 5 1-1274 500 5 5 1-1278 500 5 5 1-1279 500 55 1-1422 500 5 5 1-1431 500 5 5 1-1441 500 5 5 1-1451 500 5 5 1-1458 5005 5 1-1540 500 5 5 1-1617 500 5 5 1-1622 500 5 5 1-1627 500 5 5 1-1638500 5 5 1-1639 500 5 5 1-1641 500 5 5 1-1650 500 5 5 1-1655 500 5 51-1663 500 5 5 1-1665 500 5 5 1-1670 500 5 5 1-1673 500 5 5 1-1678 500 55 1-1679 500 5 5 1-1680 500 5 5 1-1681 500 5 5 1-1682 500 5 5 1-1683 5005 5 1-1691 500 5 5 1-1701 500 5 5 1-1718 500 5 5 1-1719 500 5 5 1-1722500 5 5 1-1732 500 5 5 1-1748 500 5 5 1-1780 500 5 5 1-1781 500 5 51-1782 500 5 5 1-1783 500 5 5 1-1785 500 5 5 2-203  500 5 5 2-251  500 55 2-328  500 5 5 2-583  500 5 5 2-631  500 5 5 2-708  500 5 5 2-821  5005 5 3-139  500 5 5 4-434  500 5 5 4-451  500 5 5 1-344  2000 5 5 1-981 2000 5 5 1-1689 2000 5 5 1-1720 2000 5 5 1-1721 2000 5 5

TEST EXAMPLE 2 Foliar Treatment on Upland Fields

[0961] Cylindrical plastic pots of 10 cm in diameter and 10 cm in depthwere filled with soil, in which the seeds of barnyardgrass (Echinochloacrus-galli), entireleaf morningglory (Ipomoea hederacea var.integriuscula), and velvetleaf (Abutilon theophrasti) were sowed, andthe test plants were grown in a greenhouse for 19 days. Each of the testcompounds listed below was formulated into an emulsifiable concentrateaccording to Formulation Example 2, which “,as diluted with watercontaining a spreading agent to a prescribed concentration. The dilutionwas uniformly sprayed over the foliage of the test plants with a sprayerat a volume of 1000 liters per hectare. After the application, the testplants were grown in the greenhouse for 19 days, and the herbicidalactivity was examined. The results are shown in Table 7. TABLE 7Application amount of active Herbicidal activity Test ingredientEntireleaf compound (g/ha) Barnyardgrass morningglory Velvetleaf 1-369 32 5 5 5 1-420  32 5 5 5 1-439  32 4 5 5 1-482  32 5 5 5 1-486  32 4 5 51-487  32 5 5 5 1-491  32 5 5 5 1-495  32 5 5 5 1-496  32 5 5 5 1-499 32 5 5 5 1-503  32 5 5 5 1-576  32 5 5 5 1-577  32 5 5 5 1-579  32 5 5 51-581  32 5 5 5 1-584  32 5 5 5 1-585  32 5 5 5 1-625  32 5 5 5 1-641 32 5 5 5 1-642  32 5 5 5 1-1057 32 5 5 5 1-1076 32 4 5 5 1-1123 32 4 5 51-1124 32 5 5 5 1-1140 32 5 5 5 1-1141 32 4 5 5 1-1213 32 5 5 5 1-121432 5 5 5 1-1221 32 5 5 5 1-1222 32 5 5 5 1-1226 32 5 5 5 1-1279 32 5 5 51-1422 32 5 5 5 1-1431 32 5 5 5 1-1441 32 5 5 5 1-1458 32 5 5 5 1-154032 5 5 5 1-1665 32 5 5 5 1-1670 32 5 5 5 1-1673 32 5 5 5 1-1678 32 5 5 51-1679 32 5 5 5 1-1680 32 5 5 5 1-1681 32 5 5 5 1-1682 32 5 5 5 1-168332 5 5 5 1-1701 32 5 5 5 1-1732 32 5 5 5 1-1780 32 5 5 5 1-1783 32 5 5 52-203  32 4 5 5 2-251  32 5 5 5 2-583  32 4 5 5 2-631  32 5 5 5 2-821 32 5 5 5 4-434  32 5 5 5

TEST EXAMPLE 3 Soil Surface Treatment on Upland Fields

[0962] Cylindrical plastic pots of 10 cm in diameter and 10 cm in depthwere filled with soil, in which the seeds of entireleaf morningglory(Ipomoea hederacea var. integriuscula) and velvetleaf (Abutilontheophrasti) were sowed. Each of the test compounds listed below wasformulated into an emulsifiable concentrate according to FormulationExample 2, which was diluted with water to a prescribed concentration.The dilution was uniformly sprayed over the soil surface in the potswith a sprayer at a volume of 1000 liters per hectare. After theapplication, the test plants were grown in a greenhouse for 19 days, andthe herbicidal activity was examined. The results are shown in Table 8.TABLE 8 Application amount of Herbicidal activity Test active ingredientEntireleaf compound (g/ha) morningglory Velvetleaf 1-347 500 5 5 1-332500 5 5 1-335 500 5 5 1-338 500 5 5 1-353 500 5 5 1-367 500 5 5 1-369500 5 5 1-391 500 5 5 1-392 500 5 5 1-398 500 5 5 1-420 500 5 5 1-439500 5 5 1-449 500 5 5 1-456 500 5 5 1-474 500 5 5 1-475 500 5 5 1-476500 5 5 1-482 500 5 5 1-486 500 5 5 1-487 500 5 5 1-491 500 5 5 1-495500 5 5 1-496 500 5 5 1-497 500 5 5 1-498 500 5 5 1-499 500 5 5 1-500500 5 5 1-501 500 5 5 1-503 500 5 5 1-504 500 5 5 1-511 500 5 5 1-576500 5 5 1-577 500 5 5 1-579 500 5 5 1-581 500 5 5 1-584 500 5 5 1-585500 5 5 1-587 500 5 5 1-621 500 5 5 1-625 500 5 5 1-641 500 5 5 1-642500 5 5  1-1028 500 5 5  1-1029 500 5 5  1-1035 500 5 5  1-1057 500 5 5 1-1066 500 5 5  1-1076 500 5 5  1-1093 500 5 5  1-1113 500 5 5  1-1123500 5 5  1-1124 500 5 5  1-1133 500 5 5  1-1140 500 5 5  1-1141 500 5 5 1-1213 500 5 5  1-1214 500 5 5  1-1221 500 5 5  1-1222 500 5 5  1-1226500 5 5  1-1279 500 5 5  1-1422 500 5 5  1-1431 500 5 5  1-1441 500 5 5 1-1451 500 5 5  1-1458 500 5 5  1-1540 500 5 5  1-1617 500 5 5  1-1622500 5 5  1-1627 500 5 5  1-1638 500 5 5  1-1639 500 5 5  1-1641 500 5 5 1-1650 500 5 5  1-1655 500 5 5  1-1663 500 5 5  1-1665 500 5 5  1-1670500 5 5  1-1673 500 5 5  1-1678 500 5 5  1-1679 500 5 5  1-1680 500 5 5 1-1681 500 5 5  1-1682 500 5 5  1-1683 500 5 5  1-1691 500 5 5  1-1780500 5 5  1-1781 500 5 5  1-1782 500 5 5  1-1783 500 5 5  1-1785 500 5 52-203 500 5 5 2-251 500 5 5 2-328 500 5 5 2-583 500 5 5 2-631 500 5 52-708 500 5 5 2-821 500 5 5 4-434 500 5 5

TEST EXAMPLE 4 Flooding Treatment on Paddy Fields

[0963] Cylindrical plastic pots of 9 cm in diameter and 11 cm in depthwere filled with soil, in which the seeds of barnyardgrass (Echinochloaoryzicola) were sowed. These pots were flooded to form a paddy field,and the test plants were grown in a green-house for 7 days. Each of thetest compounds listed below was formulated into an emulsifiableconcentrate according to Formulation Example 2, which was diluted withwater to a prescribed concentration. The dilution was applied to thewater surface in the pots at a volume of 50 liters per hectare. Afterthe application, the test plants were grown in the greenhouse for 19days, and the herbicidal activity was examined. The results are shown inTable 9. TABLE 9 Application amount of Test active ingredient Herbicidalactivity compound (g/ha) Barnyardgrass 1-332  250 5 1-335  250 5 1-338 250 5 1-347  250 5 1-353  250 5 1-367  250 5 1-369  250 5 1-391  250 51-392  250 5 1-398  250 5 1-420  250 5 1-439  250 5 1-449  250 5 1-456 250 5 1-474  250 5 1-475  250 5 1-476  250 5 1-482  250 5 1-483  250 51-486  250 5 1-487  250 5 1-491  250 5 1-495  250 5 1-496  250 5 1-497 250 5 1-498  250 5 1-499  250 5 1-500  250 5 1-501  250 5 1-503  250 51-504  250 5 1-511  250 5 1-576  250 5 1-577  250 5 1-579  250 5 1-581 250 5 1-584  250 5 1-585  250 5 1-586  250 5 1-587  250 5 1-621  250 51-625  250 5 1-641  250 5 1-642  250 5 1-1025 250 5 1-1028 250 5 1-1029250 5 1-1035 250 5 1-1057 250 5 1-1066 250 5 1-1076 250 5 1-1086 250 51-1093 250 5 1-1113 250 5 1-1123 250 5 1-1124 250 5 1-1133 250 5 1-1140250 5 1-1141 250 5 1-1213 250 5 1-1214 250 5 1-1221 250 5 1-1222 250 51-1226 250 5 1-1274 250 5 1-1278 250 5 1-1279 250 5 1-1422 250 5 1-1431250 5 1-1441 250 5 1-1451 250 5 1-1458 250 5 1-1540 250 5 1-1617 250 51-1622 250 5 1-1627 250 5 1-1638 250 5 1-1639 250 5 1-1641 250 5 1-1650250 5 1-1655 250 5 1-1663 250 5 1-1665 250 5 1-1670 250 5 1-1673 250 51-1678 250 5 1-1679 250 5 1-1680 250 5 1-1681 250 5 1-1682 250 5 1-1683250 5 1-1687 250 5 1-1691 250 5 1-1701 250 5 1-1718 250 5 1-1719 250 51-1722 250 5 1-1732 250 5 1-1748 250 5 1-1780 250 5 1-1781 250 5 1-1782250 5 1-1783 250 5 1-1785 250 5 2-203  250 5 2-251  250 5 2-328  250 52-583  250 5 2-631  250 5 2-708  250 5 2-821  250 5 3-139  250 5 4-434 250 5 4-451  250 5 1-344  500 5 1-1690 500 5 1-1720 500 5 1-1721 500 5

TEST EXAMPLE 5 Foliar Treatment on Upland Fields

[0964] Plastic pots of 25×18 cm² in area and 7 cm in depth were filledwith soil, in which the seeds of soybean (Glycine max), corn (Zea mays),entireleaf morningglory (Ipomoea hederacea var. integriuiscula), commoncocklebur (Xanthium pensylvanicum), common ragweed (Ambrosiaartemisiifolia), and common lambsquarters (Chenopodium album) weresowed, and the test plants were grown for 16 days. Each of the testcompounds listed below was formulated into an emulsifiable concentrateaccording to Formulation Example 2, which was diluted with water to aprescribed concentration. The dilution was uniformly sprayed over thefoliage of the test plants with a sprayer at a volume of 1000 liters perhectare. At this time, the unfavorable weeds and crop plants, althoughtheir growth state was different depending upon the weed species, wereat the 1- to 4-leaf stage, and the plant height was 5 to 20 cm. After 18days from the application, the herbicidal activity and phytotoxicitywere examined. The results are shown in Table 10. This test was made ina greenhouse over the entire period. TABLE 10 Appli- cation amount ofHerbicidal activity and phytotoxicity active Com- Entire- Com- Com- Testingre- mon leaf mon mon comp- dient Soy- cock- morning- rag- lambs- ound(g/ha) Corn bean lebur glory weed quarters 1-495 63 1 1 5 5 5 5 1-496 631 1 5 5 5 5 1-499 63 1 1 5 5 5 4 1-503 63 1 2 5 5 5 5 1-577 63 1 2 5 5 55

TEST EXAMPLE 6 Foliar Treatment on Upland Fields

[0965] Plastic pots of 16×11 cm² in are and 7 cm in depth were filledwith soil, in which the seeds of wheat (Triticum aestivum), palesmartweed (Polygonum lapathifolium), catchweed bedstraw (Galiumaparine), and common chickweed (Stellaria media) were sowed, and thetest plants were grown for 29 days. Each of the test compounds listedbelow was formulated into an emulsifiable concentrate according toFormulation Example 2. which was diluted with water to a prescribedconcentration. The dilution was uniformly sprayed over the foliage ofthe test plants with a sprayer at a volume of 1000 liters per hectare.At this time, the unfavorable weeds and crop plants, although theirgrowth state was different depending upon the weed species, were at the1- to 4-leaf stage, and the plant height was 5 to 15 cm. After 25 daysfrom the application, the herbicidal activity and phytotoxicity wereexamined. The results are shown in Table 11. This test was made in agreenhouse over the entire period. TABLE 11 Application amount ofHerbicidal activity and phytotoxicity active Pale Catch- Common Testingredient smart- weed chick- compound (g/ha) Wheat weed bedstraw weed1-439 63 1 5 5 5 1-482 63 1 5 5 5 1-486 63 1 5 5 5 1-496 63 0 4 5 4 1-1076 63 1 5 5 5  1-1123 63 1 5 5 5  1-1441 63 1 5 5 5

TEST EXAMPLE 7 Soil Surface Treatment on Upland Fields

[0966] Plastic pots of 25×18 cm² in area and 7 cm in depth were filledwith soil, in which the seeds of soybean (Glycine max), corn (Zea mays),common lambsquarters (Chenopodium album), slender amaranth (Amaranthusgracilis), and pale smartweed (Polygonum lapathifolium) were sowed. Eachof the test compounds listed below was formulated into an emulsifiableconcentrate according to Formulation Example 2, which was diluted withwater to a prescribed concentration. The dilution was uniformly sprayedover the soil surface in the pots with a sprayer at a volume of 1000liters per hectare. After the application. the test plants were grown ina greenhouse for 19 days, and the herbicidal activity and phytotoxicitywere examined The results are shown in Table 12. TABLE 12 Applicationamount of Herbicidal activity and phytotoxicity Test active Common Palecom- ingredient Soy- lambs- Slender smart- pound (g/ha) bean Cornquarters amaranth weed 1-511 63 1 0 5 5 5 1-642 63 1 0 5 5 5  1-1279 630 1 5 5 5  1-1691 63 0 1 5 5 5 2-203 63 2 2 5 5 5 2-631 63 1 3 5 5 5

1. A compound of the formula:

wherein R¹ is C₁-C₃ haloalkyl; R² and R³ are the same or different andare hydrogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, or C₁-C₃ alkoxy C₁-C₃ alkyl;and Q is [Q-1, [Q-2], [Q-3], [Q-4], or [Q-5] of the formula;

wherein X is hydrogen or halogen; Y is halogen. nitro, cyano, ortrifluoromethyl; Z¹ is oxygen. sulfur, or NH; Z² is oxygen or sulfur; nis 0 or 1; B is hydrogen, halogen, nitro, cyano, chlorosulfonyl, OR¹⁰.SR¹⁰, SO₂—OR¹⁰, N(R¹¹)R¹², SO₂N(R¹¹)R¹², NR¹¹(COR¹³), NR¹¹(SO₂R¹⁴),N(SO₂R¹⁴)—(SO₂R¹⁵), N(SO₂R¹⁴)(COR¹³), NHCOOR¹³, COOR¹⁰, CON(R¹¹)R¹²,CSN(R¹¹)R¹², COR¹⁶,CR¹⁷═CR¹⁸COR¹⁶,CR¹⁷═CR¹⁸COOR³CR¹⁷═CR⁸CON(R¹)R¹²,CH₂CH WCOOR¹³, CR₂CHWCON(R¹¹)R¹², CR¹⁷═NOR³³,CR¹⁷═NN(R¹¹)R¹², CR¹⁷(Z²-R³⁴)₂, OCO₂R¹⁹, or OCOR¹⁹; R⁴ is hydrogen orC₁-C₃ alkyl; R⁵ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈cycloalkylalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆haloalkynyl, cyano C₁-C₆ alkyl, C₂-C₈ alkoxyalkyl, C₃-C₈alkoxyalkoxyalkyl, carboxy C₁-C₆ alkyl, (C₁-C₆ alkoxy)-carbonyl C₁-C₆alkyl, {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkyl, (C₃-C₈cycloalkoxy)carbonyl C₁-C₆ alkyl, CH₂CON(R¹¹)R¹², CH₂COON(R¹¹)R¹²,CH(C₁-C₄ alkyl)CON(R¹¹)R¹², CH(C₁-C₄ alkyl)COON(R¹¹)R¹², C₂-C₈alkylthioalkyl, or hydroxy C₁-C₆ alkyl; R⁶ is C₁-C₆ alkyl, C₁-C₆haloalkyl, formyl, cyano, carboxyl, hydroxy C₁-C₆ alkyl, C₁-C₆ alkoxyC)—C₆ alkyl, C₁-C₆ alkoxy C₁-C₆ alkoxy C₁-C₆ alkyl, (C₁-C₆alkyl)carbonyloxy C₁-C₆ alkyl, (C₁-C₆ haloalkyl)carbonyloxy C₁-C₆ alkyl,(C₁-C₆ alkoxy)carbonyl, or (C₁-C₆ alkyl)carbonyl; R⁷ is hydrogen orC₁-C₆ alkyl; and R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, hydroxyC₁-C₆ alkyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, (C₁-C₅alkyl)carbonyloxy C₁-C₆ alkyl, (C₁-C₆ haloalkyl)carbonyloxy C₁-C₆ alkyl,carboxyl, carboxy C₁-C₆ alkyl, (C₁-Cg alkoxy)-carbonyl, (C₁-C₆haloalkoxy)carbonyl, (C₃-C₁₀ cycloalkoxy)carbonyl, (C₃-C₈alkenyloxy)carbonyl. (C₃-Cg alkynyloxy)carbonyl, aminocarbonyl, (C₁-C₆alkyl)aminocarbonyl. di(C₁-C₆ alkyl)aminocarbonyl, (C₁-C₆alkyl)aminocarbonyloxy C₁-C₆ alkyl, or di(C₁-C₆ alkyl)aminocarbonyloxyC₁-C₆ alkyl; wherein R¹⁰ is hydrogen, C₁-C₆ alkyl. C₁-C₆ haloalkyl,C₃-C₈ cycloalkyl, benzyl. C₁-C₆ alkenyl, C₁-C₆ haloalkenyl. C₁-C₆alkynyl, C₃-C₆ haloalkynyl, cyano C₁-C₆ alkyl, C₂-C₈ alkylthioalkylC₂-C₈ carboxy C₁-C₆ alkyl, (C₁-C₈ alkoxy)carbonyl C₁-C₆ alkyl, (C₁-C₆haloalkoxy)carbonyl C₁-C₆ alkyl, {(C₁-C₄ alkoxy) C₁-C₄ alkoxy)carbonylC₁-C₆ alkyl, (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl, (C₁-C₆alkyl)carbonyl C₁-C₆ alkyl, (C₁-C₆ haloalkyl)carbonyl C₁-C₆ alkyl,{(C₁-C₄ alkoxy) C₁-C₄ alkyl}carbonyl C₁-C₆ alkyl, (C₃-Cgcycloalkyl)carbonyl C₁-C₆ alkyl, CH₂CON—(R¹¹)R¹², CH₂COON(R¹¹)R¹²,CH(C₁-C₄ alkyl)CON(R¹¹ )R¹², CH(C₁-C₄ alkyl)-COON(R¹¹)R¹², ((C₂-C₆alkoxy)carbonyl C₁-C₆ alkyl]oxycarbonyl C₁-C₆ alkyl, or hydroxy C₁-C₆alkyl; R¹¹ and R¹² are independently hydrogen, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, cyano C₁-C₆ alkyl, C₂-C₈alkoxyalkyl, C₂-C₈ alkylthioalkyl, carboxy C₁-C₆ alkyl, (C₁-C₆alkoxy)carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkoxy)-carbonyl C₁-C₆ alkyl,{(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkyl, or R¹¹ and R¹² arecombined together to form tetramethylene, pentamethylene, orethyleneoxyethylene; R¹³ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₈ cycloalkyl, or C₃-C₆ alkenyl; R¹⁴ and R¹⁵ are independently C₁-C₆alkyl, C₁-C₆ haloalkyl, or phenyl optionally substituted with methyl ornitro; R¹⁶ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl,C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, C₂-C₈ alkoxyalkyl,or hydroxy C₁-C₆ alkyl; R¹⁷ and R¹⁸ are independently hydrogen or C₁-C₆alkyl; R¹⁹ is C₁-C₆ alkyl; R³³ is hydrogen, C₁-C₆ alkyl. C₁-C₆haloalkyl, C₃-C₈ cycloalkyl. C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆alkynyl, C₃-C₆ haloalkynyl, cyano C₁-C₆ alkyl, or (C₁-C₆ alkoxy)carbonylC₁-C₆ alkyl; R³⁴ is C₁-C₆ alkyl, or two R³⁴'s are combined together toform (CH₂)₂ or (CH)₃; and W is hydrogen, chlorine, or bromine.
 2. Acompound according to claim 1, wherein R¹ is trifluoromethyl.
 3. Acompound according to claim 1, wherein R² is hydrogen or C₁-C₃ alkyl,and R³ is hydrogen or C₁-C₃ alkyl.
 4. A compound according to claim 1,wherein R¹ is trifluoromethyl, R² is hydrogen or C₁-C₃ alkyl, and R³ ishydrogen or C₁-C₃ alkyl.
 5. A compound according to claim 1, 2, 3, or 4,wherein Q is [Q-1].
 6. A compound according to claim 1, 2, 3, or 4,wherein Q is [Q-2].
 7. A compound according to claim 1, 2, 3, or 4,wherein Q is [Q-3].
 8. A compound according to claim 1, 2, 3, or 4,wherein Q is [Q-4].
 9. A compound according to claim 1, 2, 3, or 4,wherein Q is [Q-5].
 10. A compound according to claim 5, wherein B isOR¹⁰.
 11. A compound according to claim 5, wherein B is SR¹⁰.
 12. Acompound according to claim 5, wherein B is N(R¹¹)R¹².
 13. A compoundaccording to claim 5, wherein B is NR¹¹(SO₂R¹⁴).
 14. A compoundaccording to claim 5, wherein B is COOR¹⁰.
 15. A compound according toclaim 5, wherein X is fluorine and Y is chlorine.
 16. A compoundaccording to claim 5, wherein X is fluorine, Y is chlorine, and B isOR¹⁰.
 17. A compound according to claim 6, wherein Z¹ is oxygen and nis
 1. 18. A compound according to claim 1, which is7-fluoro-6-(5-trifluoro-methyl-3-pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one(compound 2-631).
 19. A compound according to claim 1, which is7-fluoro-6-(4-methyl-5-trifluoromnethyl-3-pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one(compound 2-251).
 20. A compound according to claim 1, which is6-(5-trifluoromethyl-3-pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one(compound 2-583).
 21. A compound according to claim
 1. which is6-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one(compound 2-203).
 22. A compound according to claim 1, which is2-(4-chloro-2-fluoro-5-isopropoxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one(compound 1-476).
 23. A compound according to claim 1, which is2-(4-chloro-2-fluoro-5-methoxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one(compound 1-474).
 24. A compound according to claim 1, which is2-(4-chloro-2-fluoro-5-ethoxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one(compound 1-475).
 25. A compound according to claim 1, which is2-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one(compound 1-486).
 26. A compound according to claim 1, which is methyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate(compound 1-495).
 27. A compound according to claim 1, which is ethyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate(compound 1-496).
 28. A compound according to claim 1, which is propyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate(compound 1-497).
 29. A compound according to claim 1, which isisopropyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate(compound 1-500).
 30. A compound according to claim 1, which is butyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate(compound 1-498).
 31. A compound according to claim 1, which is pentyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate(compound 1-499).
 32. A compound according to claim 1, which iscyclopentyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate(compound 1-501)
 33. A compound according to claim 1, which is ethyl2-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxy}propionate (compound 1-504).
 34. A compound according to claim 1, whichis methyl2-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxy}propionate(compound 1-503).
 35. A compound according to claim 1, which is ethyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylthioacetate(compound 1-577).
 36. A compound according to claim 1, which is methyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylthioacetate(compound 1-576).
 37. A compound according to claim 1, which is ethyl2-(2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate(compound 1-585).
 38. A compound according to claim 1, which is methyl2-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate(compound 1-584).
 39. A compound according to claim 1, which is methyl2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenoxy}propionate(compound 1-1140).
 40. A compound according to claim 1, which is ethyl2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenoxy}propionate(compound 1-1141).
 41. A compound according to claim 1, which is ethyl2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthioacetate(compound 1-1214).
 42. A compound according to claim 1 which is methyl2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthioacetate(compound 1-1213)
 43. A compound according to claim
 1. which is ethyl2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate(compound 1-1222).
 44. A compound according to claim 1, which is methyl2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate(compound 1-1221).
 45. A compound according to claim 1, which isisopropyl2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate(compound 1-1226).
 46. A compound according to claim 1, which is ethyl2-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylamino}propionate(compound 1-420).
 47. A compound according to claim 1, which is ethyl2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylamino}propionate(compound 1-1057).
 48. A compound according to claim 1, which isN-(2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylmethanesulfonamide (compound 1-367).
 49. A compound according to claim1, which isN-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenyl}chloromethanesulfonamide (compound 1-369).
 50. A compoundaccording to claim 1, which isN-{2-chloro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenyl}methanesulfonamide(compound 1-398).
 51. A compound according to claim 1 which is methyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)benzoate(compound 1-641).
 52. A compound according to claim 1, which is ethyl2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)benzoate(compound 1-642)
 53. A compound according to claim 1, which is ethyl2-chloro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)benzoate(compound 1-621)
 54. A compound according to claim 1, which is isopropyl2-chloro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)benzoate(compound 1-625)
 55. A compound according to claim 1, which is2-(4-chloro-2-fluoro-5-propargyloxyphenyl)-6-methyl-5-trifluoromethylpyridazin-3-one(compound 1-1 441).
 56. A herbicidal composition comprising aherbicidally effective amount of the compound according to claim
 1. andan inert carrier or diluent.
 57. A method for controlling unfavorableweeds, which comprises applying a herbicidally effective amount of thecompound according to claim 1 to an area where the unfavorable weedsgrow or will grow.
 58. Use of the compound according to claim 1 as aherbicide.
 59. A compound of the formula;

wherein R³ is as defined in claim 1, and Q¹ is [Q¹-1], [Q-2], [Q¹-3],[Q-4], or [Q-5] of the formula:

wherein X, Y, Z¹, Z², n, R⁴, R⁵, R⁷, and R⁸ are as defined in claim 1;B¹ is hydrogen halogen nitro cyano, OR²⁷. SR²⁷, SO₂OR²⁷, NR¹(R¹²),SO₂NR¹¹(R¹²), NR¹¹(COR¹³). NR¹¹(SO₂R⁴), N(SO₂R⁴)(SO₂R¹⁵), N(SO₂R¹⁴)(COR¹³). NHCOOR¹³, COOR²⁷, CONR” (R¹²), CSNR¹¹(R¹²), CR¹⁷═CR¹⁸COOR¹³,CR¹⁷═CR¹⁸CONR¹¹(R¹²) CH₂CHWCOOR¹³. CH₂CHWCONR¹¹(R¹²), CR¹⁷═N—OR³³,CR¹⁷═NNR¹¹(R¹²). CR¹⁷(Z²R³⁴)₂, OCO₂R⁹ or OCOR¹⁹, and R⁹ is C₁-C₆ alkyl,C₁-C₆ haloalkyl, cyano, carboxyl, hydroxy C₁-C₆ alkyl, C₁-C₆ alkoxyC₁-C₆ alkyl, C₁-C₆ alkoxy C₁-C₆ alkoxy C₁-C₆ alkyl, (C₁-C₆ alkyl)carbonyloxy C₁-C₆ alkyl, (C₁-C₆ haloalkyl)carbonyloxy C₁-C₆ alkyl,(C₁-C₆ alkoxy) carbonyl, or (C₁-C₆ alkyl)carbonyl; wherein R²⁷ ishydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, benzyl, C₃-C₆alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, cyanoC₁-C₆ alkyl, C₂-C₈ alkoxyalkyl, C₂-C₈ alkylthioalkyl, carboxy C₁-C₆alkyl, (C₁-C₈ alkoxy)carbonyl C₁-C₆ alkyl, (C₁-C₆ haloalkoxy)carbonylC₁-C₆ alkyl, {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkyl, (C₃-C₈cycloalkoxy)carbonyl C₁-C₆ alkyl, CH₂CO—N(R¹¹)R¹², CH₂COON(R¹¹)R¹²CH(C₁-C₄ alkyl)CON(R¹¹)R¹², CH(C₁-C₄ alkyl) COON(R¹¹)R¹², {(C₁-C₆alkoxy)carbonyl C₁-C₆ alkyl}oxycarbonyl C₁-C₆ alkyl, or hydroxy C₁-C₆alkyl; and R¹¹, R¹², R¹³, R¹⁴, R¹⁵ R⁷; —R¹⁸, R¹⁹, R³³ R³⁴, and Z² are asdefined in claim 1.